Abstract
The production of controlled release systems for Diuron aims to reduce some disadvantages of its conventional application and to diminish the associated environmental pollution. In this work, a matrix of urea–formaldehyde containing micro-encapsulated Diuron (Diuron–UF) is proposed to that purpose. The results of the morphology and distribution of particles sizes are expected to promote permeability allowing a water flux and the release of the pesticide. The possible interactions between the UF matrix and Diuron were investigated using experimental and theoretical techniques. The obtained results strongly suggest that the Diuron–UF interactions are weak enough to assure easy release. The shifts in the IR bands are modest, which is in line with the proposal that the interactions arise from H bonding and do not involve the formation of chemical bonds. The in vitro assays showed that the investigated material releases small amounts of the active component for extended periods of time. This behavior is expected to allow a large assimilation of the pesticide by plants, at the same time that it would prevent—or at least reduce—the environmental pollution caused by the Diuron degradation products. The gathered data combined indicate that Diuron–UF materials can be used as “intelligent pesticides”.
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Atta S, Paul A, Banerjee R, Bera M, Ikbal M, Dhara D, Singh NDP (2015) Photoresponsive polymers based on a coumarin moiety for the controlled release of pesticide 2,4-D. RSC Adv 5:99968–99975
Barrett K, Jaward FM (2012) A review of endosulfan, dichlorvos, diazinon, and diuron—pesticides used in Jamaica. Int J Environ Health Res 22:481–499
Bibi S, Nawaz M, Yasin T, Riaz M (2016) Chitosan/CNTs nanocomposite as green carrier material for pesticides controlled release. J Polym Res 23:154. doi:10.1007/s10965-016-1055-9
Campos EVR, de Oliveira JL, Fraceto LF, Singh B (2015) Polysaccharides as safer release systems for agrochemicals. Agron Sustain Dev 35:47–66
Castanon-Gonzalez JH, Galindez-Mayer J, Ruiz-Ordaz N, Rocha-Martinez L, Pena-Partida JC, Marron-Montiel E, Santoyo-Tepole F (2016) Biodegradation of the herbicide Diuron in a packed bed channel and a double biobarrier with distribution of oxygenated liquid by airlift devices: influence of oxygen limitation. N Biotechnol 33:7–15
Chevillard A, Angellier-Coussy H, Guillard V, Gontard N, Gastaldi E (2012) Investigating the biodegradation pattern of an ecofriendly pesticide delivery system based on wheat gluten and organically modified montmorillonites. Polym Degrad Stab 97:2060–2068
Da Rocha MS, Arnold LL, De Oliveira M, Catalano SMI, Cardoso APF, Pontes MGN, Ferrucio B, Dodmane PR, Cohen SM, De Camargo JLV (2014) Diuron-induced rat urinary bladder carcinogenesis: mode of action and human relevance evaluations using the International Programme on Chemical Safety framework. Crit Rev Toxicol 44:393–406
El Imache A, Dahchour A, Elamrani B, Dousset S, Pozzonni F, Guzzella L (2009) Leaching of Diuron, Linuron and their main metabolites in undisturbed field lysimeters. J Environ Sci Health B 44:31–37
Fesssi H, Marty JP, Puisieux F, Carstensen JT (1978) The Higu Chi square root equation applied to matrices with high content of soluble drug substance. Int J Pharm 1:265–274
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark MJ, Heyd J, Brothers EN, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09. Gaussian Inc, Wallingford
Giacomazzi S, Cochet N (2004) Environmental impact of diuron transformation: a review. Chemosphere 56:1021–1032
González-Hurtado M, Díaz MIH, Dupeyrón-Martell D, Rieumont-Briones J, Rodríguez-Acosta C, Cuesta E, Sardiña C (2007) Síntesis y comportamiento de un material polimérico aplicado como recubrimiento en un fertilizante de liberación controlada. Rev Iberoam Polim 8:275–286
Gutiérrez JM, González C, Maestro A, Solè I, Pey CM, Nolla J (2008) Nano-emulsions: new applications and optimization of their preparation. Curr Opin Colloid Interface Sci 13:245–251
He S, Zhang W, Li D, Li P, Zhu Y, Ao M, Li J, Cao Y (2013) Preparation and characterization of double-shelled avermectin microcapsules based on copolymer matrix of silica-glutaraldehyde-chitosan. J Mater Chem B 1:1270–1278
Hedaoo RK, Gite VV (2014) Renewable resource-based polymeric microencapsulation of natural pesticide and its release study: an alternative green approach. RSC Adv 4:18637–18644
Hill CG, Hedren AM, Myers GE, Koutsky JA (1984) Raman spectroscopy of urea–formaldehyde resins and model compounds. J Appl Polym Sci 29:2749–2762
Hurtado MG, Briones JR, Owen PQ, Bartolo-Perez P, Soares BG, Cossa MM (2015) Ferlent (R)—a controlled release fertilizer produced from a polymeric material with agronomic benefits. Environ Eng Manag J 14:2913–2917
Ikeda S, Suzuki K, Kawahara M, Noshiro M, Takahashi N (2014) An assessment of urea-formaldehyde fertilizer on the diversity of bacterial communities in onion and sugar beet. Microbes Environ 29:231–234
Innerebner G, Knief C, Vorholt JA (2011) Protection of Arabidopsis thaliana against leaf-pathogenic Pseudomonas syringae by Sphingomonas strains in a controlled model system. Appl Environ Microbiol 77:3202–3210
Jahns T, Ewen H, Kaltwasser H (2003) Biodegradability of urea-aldehyde condensation products. J Polym Environm 11:155–159
Kah M, Hofmann T (2014) Nanopesticide research: current trends and future priorities. Environ Int 63:224–235
Kumar S, Bhanjana G, Sharma A, Sidhu MC, Dilbaghi N (2014) Synthesis, characterization and on field evaluation of pesticide loaded sodium alginate nanoparticles. Carbohydr Polym 101:1061–1067
Kumar S, Chauhan N, Gopal M, Kumar R, Dilbaghi N (2015) Development and evaluation of alginate-chitosan nanocapsules for controlled release of acetamiprid. Int J Biol Macromol 81:631–637
Li ZZ, Xu SA, Wen LX, Liu F, Liu AQ, Wang Q, Sun HY, Yu W, Chen JF (2006) Controlled release of avermectin from porous hollow silica nanoparticles: influence of shell thickness on loading efficiency, UV-shielding property and release. J Control Release 111:81–88
Li D, Liu B, Yang F, Wang X, Shen H, Wu D (2016) Preparation of uniform starch microcapsules by premix membrane emulsion for controlled release of avermectin. Carbohydr Polym 136:341–349
Lin CC, Chu YM, Chang HC (2013) In situ encapsulation of antibody on TiO2 nanowire immunosensor via electro-polymerization of polypyrrole propylic acid. Sens Actuators B Chem 187:533–539
Liu Y, Tong Z, Homme RKP (2008) Stabilized polymeric nanoparticles for controlled and efficient release of bifenthrin. Pest Manag Sci 64:808–812
Liu B, Wang Y, Yang F, Wang X, Shen H, Cui H, Wu D (2016) Construction of a controlled-release delivery system for pesticides using biodegradable PLA-based microcapsules. Colloids Surf B Biointerfaces 144:38–45
Lubkowski K (2014) Coating fertilizer granules with biodegradable materials for controlled fertilizer release. Environ Eng Manag J 13:2573–2581
Margni M, Rossier D, Crettaz P, Jolliet O (2002) Life cycle impact assessment of pesticides on human health and ecosystems. Agric Ecosyst Environ 93:379–392
Marques R, Oehmen A, Carvalho G, Reis MAM (2015) Modelling the biodegradation kinetics of the herbicide propanil and its metabolite 3,4-dichloroaniline. Environ Sci Pollut Res Int 22:6687–6695
Merrick JP, Moran D, Radom L (2007) An evaluation of harmonic vibrational frequency scale factors. J Phys Chem A 111:11683–11700
Metz JG, Pakrasi HB, Seibert M, Arntzer CJ (1986) Evidence for a dual function of the herbicide-binding D1 protein in photosystem II. FEBS Lett 205:269–274
Mogul MG, Akin H, Hasirci N, Trantolo DJ, Gresser JD, Wise DL (1996) Controlled release of biologically active agents for purposes of agricultural crop management. Resour Conserv Recycl 16:289–320
Moorthy MS, Bharathiraja S, Manivasagan P, Oh Y, Jang B, Phan TTV, Oh J (2017) Synthesis of urea-pyridyl ligand functionalized mesoporous silica hybrid material for hydrophobic and hydrophilic drug delivery application. J Porous Mater. doi:10.1007/s10934-017-0425-y
Muro-Sune N, Gani R, Bell G, Shirley I (2005) Model-based computer-aided design for controlled release of pesticides. Comput Chem Eng 30:28–41
Peppas NA, Langer R (1994) New challenges in biomaterials. Science 263:1715–1720
Peverati R, Truhlar DG (2014) Quest for a universal density functional: the accuracy of density functionals across a broad spectrum of databases in chemistry and physics. Philos Trans A Math Phys Eng Sci 372:20120476
Roy A, Singh SK, Bajpai J, Bajpai AK (2014) Controlled pesticide release from biodegradable polymers. Cent Eur J Chem 12:453–469
Saha D, Warren KE, Naskar AK (2014) Soft-templated mesoporous carbons as potential materials for oral drug delivery. Carbon 71:47–57
Singh B, Sharma DK, Kumar R, Gupta A (2010) Controlled release of thiram from neem–alginate–clay based delivery systems to manage environmental and health hazards. Appl Clay Sci 47:384–391
Song S, Liu X, Jiang J, Qian Y, Zhang N, Wu Q (2009) Stability of triazophos in self-nanoemulsifying pesticide delivery system. Colloids Surf A 350:57–62
Sun C, Shu K, Wang W, Ye Z, Liu T, Gao Y, Zheng H, He G, Yin Y (2014) Encapsulation and controlled release of hydrophilic pesticide in shell cross-linked nanocapsules containing aqueous core. Int J Pharm 463:108–114
Toyota K, Watanabe T (2013) Recent trends in microbial inoculants in agriculture. Microbes Environ 28:403–404
Vallet-Regí M, Balas F, Arcos D (2007) Mesoporous materials for drug delivery. Angew Chem Int Ed Engl 46:7548–7558
Vuilleumier S, Chistoserdova L, Lee MC, Bringel F, Lajus A, Yang Z, Gourion B, Barbe V, Chang J, Cruveiller S, Dossat C, Gillett W, Gruffaz C, Haugen E, Hourcade E, Levy R, Mangenot S, Muller E, Nadalig T, Pagni M, Penny C, Peyraud R, Robinson DG, Roche D, Rouy Z, Saenempechek C, Salvignol G, Vallenet D, Zaining W, Marx CJ, Vorholt JA, Olson MV, Kaul R, Weissenbach J, Médigue C, Lidstrom ME (2009) Methylobacterium genome sequences: a reference blueprint to investigate microbial metabolism of C1 compounds from natural and industrial sources. PLoS One 4(5):e5584. doi:10.1371/journal.pone.0005584
Yamamoto CF, Pereira EI, Mattoso LHC, Matsunaka T, Ribeiro C (2016) Slow release fertilizers based on urea/urea-formaldehyde polymer nanocomposites. Chem Eng J 287:390–397
Yearla SR, Padmasree K (2016) Exploitation of subabul stem lignin as a matrix in controlled release agrochemical nanoformulations: a case study with herbicide diuron. Environ Sci Pollut Res Int 23:18085–18098
Yi Y, Xu S, Sun H, Chang D, Yin Y, Zheng H, Xu H, Lou Y (2011) Gelation of photocrosslinkable carboxymethyl chitosan and its application in controlled release of pesticide. Carbohydr Polym 86:1007–1013
Yuan H, Li G, Yang L, Yan X, Yang D (2015) Development of melamine-formaldehyde resin microcapsules with low formaldehyde emission suited for seed treatment. Colloids Surf B Biointerfaces 128:149–154
Yuan Y, Zhang P, Schaffer A, Schmidt B (2017) 3,4-Dichloroaniline revisited: a study on the fate of the priority pollutant in a sediment-water system derived from a rice growing region in Italy. Sci Total Environ 574:1012–1020
Zhao Y, Schultz NE, Truhlar DG (2006) Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. J Chem Theory Comput 2:364–382
Zhao J, Fu X, Zhang S, Hou W (2011) Water dispersible avermectin-layered double hydroxide nanocomposites modified with sodium dodecyl sulfate. Appl Clay Sci 51:460–466
Zhu B, Liu TQ, Hu XG, Wang GX (2013) Developmental toxicity of 3,4-dichloroaniline on rare minnow (Gobiocypris rarus) embryos and larvae. Chemosphere 90:1132–1139
Acknowledgements
Dr. González-Hurtado is grateful to TWAS and CONACYT for the award of Postdoctoral Fellowship and its financial support. Dr. I. Zumeta-Dube acknowledges postdoctoral fellow from CONACYT, Project no. CB2014-235840. We gratefully acknowledge the Laboratorio de Visualización y Cómputo Paralelo at Universidad Autónoma Metropolitana-Iztapalapa for computing time, and Dr. Enelio Torres-Garcia for the helpful discussion.
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González-Hurtado, M., Rieumont-Briones, J., Castro-González, L.M. et al. Combined experimental–theoretical investigation on the interactions of Diuron with a urea–formaldehyde matrix: implications for its use as an “intelligent pesticide”. Chem. Pap. 71, 2495–2503 (2017). https://doi.org/10.1007/s11696-017-0245-1
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DOI: https://doi.org/10.1007/s11696-017-0245-1