Nanoparticles of poly(epsilon-caprolactone) containing the herbicide atrazine were prepared, characterized, and evaluated in terms of their herbicidal activity and genotoxicity. The stability of the nanoparticles was evaluated over a period of three months, considering the variables: size, polydispersion index, pH, and encapsulation efficiency. Tests on plants were performed with target (Brassica sp.) and non-target (Zea mays) organisms, and the nanoparticle formulations were shown to be effective for the control of the target species. Experiments using soil columns revealed that the use of nanoparticles reduced the mobility of atrazine in the soil. Application of the Allium cepa chromosome aberration assay demonstrated that the nanoparticle systems were able to reduce the genotoxicity of the herbicide. The formulations developed offer a useful means of controlling agricultural weeds, while at the same time reducing the risk of harm to the environment and human health. © 2014 Elsevier B.V.268 207215Hernandez, D.D., Alves, P.L.C., Pavani, M.C.M.D., Parreira, M.C., Periods of nightshade interference in processing tomato (2007) Hortic. Bras., 25, pp. 199-204Holt, J.S., Herbicides (2013) Encyclopedia of Biodiversity, pp. 87-95. , Academic Press, Waltham, S.A. Levin (Ed.)Machado, R.F., Barros, A.C.S.A., Zimmer, P.D., dos, S.A., Reflexes of the mechanism of herbicides action in seed physiologic quality and in the enzymatic activity of rice seedlings (2006) Rev. Bras. Sementes, 28, pp. 151-160Trebst, A., The mode of action oftriazine herbicides in plants (2008) Triazine Herbicides, pp. 101-110. , Elsevier, San Diego, (Chapter 8), H.M. LeBaron, J.E. McFarland, O.C. Burnside (Eds.)Nair, R., Varghese, S.H., Nair, B.G., Maekawa, T., Yoshida, Y., Kumar, D.S., Nanoparticulate material delivery to plants (2010) Plant Sci., 179, pp. 154-163Li, X., Wu, T., Huang, H., Zhang, S., Atrazine accumulation and toxic responses in maize Zea mays (2012) J. Environ. Sci., 24, pp. 203-208Bortoluzzi, E.C., dos, D., Rheinheimer, S., Gonccalves, C.S., Pellegrini, J.B., Zanella, R., Copetti, A.C., Contaminaccão de águas superficiais por agrotóxicos em fun\ccão do uso do solo numa microbacia hidrográfica de Agudo, RS (2006) Rev. Bras. Eng. Agríc. Ambient., 10, pp. 881-887Graymore, M., Stagnitti, F., Allinson, G., Impacts of atrazine in aquatic ecosystems (2001) Environ. Int., 26, pp. 483-495Hayes, T., Haston, K., Tsui, M., Hoang, A., Haeffele, C., Vonk, A., Herbicides feminization of male frogs in the wild (2002) Nature, 419, pp. 895-896Quina, F.H., Nanotecnologia e o meio ambiente: perspectivas e riscos (2004) Quím. Nova, 27, pp. 1028-1029McNeil, S.E., Nanotechnology for the biologist (2005) J. Leukoc. Biol., 78, pp. 585-594Chen, H., Yada, R., Nanotechnologies in agriculture: new tools for sustainable development (2011) Trends Food Sci. Technol., 22, pp. 585-594de, B.G., Medeiros, S., Pinheiro, A.C., Teixeira, J.A., Vicente, A.A., Carneiro-da-Cunha, M.G., Polysaccharide/protein nanomultilayer coatings: construction, characterization and evaluation of their effect on Rocha Pear (Pyrus communis L) shelf-life (2012) Food Bioprocess Technol., 5, pp. 2435-2445Loha, K.M., Shakil, N.A., Kumar, J., Singh, M.K., Srivastava, C., Bio-efficacy evaluation of nanoformulations of β-cyfluthrin against Callosobruchus maculatus (Coleoptera: Bruchidae) (2012) J. Environ. Sci. Health Part B, 47, pp. 687-691Grillo, R., dos Santos, N.Z.P., Maruyama, C.R., Rosa, A.H., de Lima, R., Fraceto, L.F., Poly(e-caprolactone)nanocapsules as carrier systems for herbicides: physico-chemical characterization and genotoxicity evaluation (2012) J. Hazard. Mater., pp. 1-9Cea, M., Cartes, P., Palma, G., Mora, M.L., Atrazine efficiency in an andisol as affected by clays and nanoclays in ethylcellulose controlled release formulations (2010) Rev. Cienc. Suelo Nutr. Veg., 10, pp. 62-77Wanyika, H., Gatebe, E., Kioni, P., Tang, Z., Gao, Y., Mesoporous silica nanoparticles carrier for urea: potential applications in agrochemical delivery systems (2012) J. Nanosci. Nanotechnol., 12, pp. 2221-2228Liu, Y., Tong, Z., Prud'homme, R.K., Stabilized polymeric nanoparticles for controlled and efficient release of bifenthrin (2008) Pest Manag. Sci., 64, pp. 808-812Canfarotta, F., Whitcombe, M.J., Piletsky, S.A., Polymeric nanoparticles for optical sensing (2013) Biotechnol. Adv., 31, pp. 1585-1599Galperin, A., Margel, D., Baniel, J., Dank, G., Biton, H., Margel, S., Radiopaque iodinated polymeric nanoparticles for X-ray imaging applications (2007) Biomaterials, 28, pp. 4461-4468Kammona, O., Kotti, K., Kiparissides, C., Celis, J.P., Fransaer, J., Synthesis of polymeric and hybrid nanoparticles for electroplating applications (2009) Electrochim. Acta, 54, pp. 2450-2457Cheng, Y., (2011), Gold Nanoparticles as Drug Delivery Vectors for Photodynamic Therapy of Cancers, Case Western Reserve UniversitySinha, V.R., Bansal, K., Kaushik, R., Kumria, R., Trehan, A., Poly-e-caprolactone microspheres and nanospheres: an overview (2004) Int. J. Pharm., 278, pp. 1-23Byun, Y., Hwang, J.B., Bang, S.H., Darby, D., Cooksey, K., Dawson, P.L., Formulation and characterization of α-tocopherol loaded poly e-caprolactone (PCL) nanoparticles (2011) LWT-Food Sci. Technol., 44, pp. 24-28Kah, M., Hofmann, T., Nanopesticide research: current trends and future priorities (2014) Environ. Int., 63, pp. 224-235Khot, L.R., Sankaran, S., Maja, J.M., Ehsani, R., Schuster, E.W., Applications of nanomaterials in agricultural production and crop protection: a review (2012) Crop Prot., 35, pp. 64-70Zhou, Z., Ye, J., Chen, L., Ma, A., Zou, F., Simultaneous determination of ropivacaine, bupivacaine and dexamethasone in biodegradable PLGA microspheres by high performance liquid chromatography (2010) Yakugaku Zasshi, 130, pp. 1061-1068Schaffazick, S.R., Guterres, S.S., de, L., Freitas, L., Pohlmann, A.R., Physicochemical characterization and stability of the polymeric nanoparticle systems for drug administration (2003) Quím. Nova, 26, pp. 726-737Korsmeyer, R.W., Gurny, R., Doelker, E., Buri, P., Peppas, N.A., Mechanisms of solute release from porous hydrophilic polymers (1983) Int. J. Pharm., 15, pp. 25-35Rao, J.P., Geckeler, K.E., Polymer nanoparticles: preparation techniques and size-control parameters (2011) Prog. Polym. Sci., 36, pp. 887-913Mohanraj, V.J., Chen, Y., Nanoparticles-a review (2007) Trop. J. Pharm. Res., 5, pp. 561-573Lemoine, D., Francois, C., Kedzierewicz, F., Preat, V., Hoffman, M., Maincent, P., Stability study of nanoparticles of poly (e-caprolactone), poly (d, l-lactide) and poly (d, l-lactide-co-glycolide) (1996) Biomaterials, 17, pp. 2191-2197de, R., Javaroni, C.A., Landgraf, M.D., Rezende, M.O.O., Behavior of the herbicides atrazine and alachlor after application on soils prepared to sugar cane plantation (1999) Quím. Nova, 22, pp. 58-64Lopes, C.M., Lobo, J.M.S., Costa, P., Modified release of drug delivery systems: hydrophilic polymers (2005) Rev. Bras. Ciênc. Farm., 41, pp. 143-154Li, B., Hu, R., Cheng, Z., Cheng, J., Xie, Y., Gui, S., Titanium dioxide nanoparticles relieve biochemical dysfunctions of fifth-instar larvae of silkworms following exposure to phoxim insecticide (2012) Chemosphere, 89, pp. 609-614Elek, N., Hoffman, R., Raviv, U., Resh, R., Ishaaya, I., Magdassi, S., Novaluron nanoparticles: formation and potential use in controlling agricultural insect pests (2010) Colloids Surf. Physicochem. Eng. Asp., 372, pp. 66-72Sarkar, D.J., Kumar, J., Shakil, N.A., Walia, S., Release kinetics of controlled release formulations of thiamethoxam employing nano-ranged amphiphilic PEG and diacid based block polymers in soil (2012) J. Environ. Sci. Health Part A Tox. Hazard. Subst. Environ. Eng., 47, pp. 1701-17124 - Atrazine (2011) Handbook of Pollution Prevention and Cleaner Production Vol. 3: Best Practices in the Agrochemical Industry, pp. 215-231. , William Andrew Publishing, OxfordMa, Y., Kuang, L., He, X., Bai, W., Ding, Y., Zhang, Z., Effects of rare earth oxide nanoparticles on root elongation of plants (2010) Chemosphere, 78, pp. 273-279Khodakovskaya, M.V., Kim, B.-S., Kim, J.N., Alimohammadi, M., Dervishi, E., Mustafa, T., Carbon nanotubes as plant growth regulators: effects on tomato growth, reproductive system, and soil microbial community (2013) Small, 9, pp. 115-123Ma, X., Geiser-Lee, J., Deng, Y., Kolmakov, A., Interactions between engineered nanoparticles (ENPs) and plants: phytotoxicity, uptake and accumulation (2010) Sci. Total Environ., 408, pp. 3053-3061Radosevich, M., Traina, S.J., Tuovinen, O.H., Atrazine mineralization in laboratory-aged soil microcosms inoculated with s-triazine-degrading bacteria (1997) J. Environ. Qual., 26, pp. 206-214Jr, M.F.K., Regulatory aspects of bound residues (chemistry) (1986) Residue Reviews, pp. 1-17. , Springer, New York, F.A. Gunther (Ed.)Guimaraes, G.L., Impactos ecológicos do uso de herbicidas ao meio ambiente (1987) Série Técnica IPEF, 4, pp. 159-180Brancalion, P.H.S., Isernhagen, I., Machado, R.P., Christoffoleti, P.J., Rodrigues, R.R., Seletividade dos herbicidas setoxidim, isoxaflutol e bentazon a espécies arbóreas nativas (2009) Pesq. Agropec. Bras. Brasília., 44, pp. 251-257Abu-Zreig, M., Rudra, R., Dickinson, W., Evans, L., Effect of surfactants on sorption of atrazine by soil (1999) J. Contam. Hydrol., 36, pp. 249-263Dan, H.A., Barroso, A.L.L., Procópio, S.O., Dan, L.G.M., Finotti, T.R., Assis, R.L., Atrazine selectivity in pearl millet (Pennisetum glaucum) (2010) Planta Daninha, 28, pp. 1117-1124de, H., Dan, A., de, A.L., Barroso, L., Finotti, T.R., de, L.G., Dan, M., de Assis, R.L., Tolerance of pearl millet cultivar ADR-300 to atrazine herbicide (2011) Rev. Ciênc. Agron., 42, pp. 193-198de Ávila, L.G., Leite, S.B., Dick, D.P., Pohlmann, A.R., Formula\ccões de atrazina em xerogéis: síntese e caracteriza\ccão (2009) Quim. Nova, 32, pp. 1727-1733de Paula, H.C., de Oliveira, E.F., Abreu, F.O., de Paula, R.C., de Morais, S.M., Forte, M.M., Esferas (beads) de alginato como agente encapsulante de oleo de croton zehntneri Pax et Hoffm (2010) Polímeros, 20, pp. 112-120Leme, D.M., Marin-Morales, M.A., Allium cepa test in environmental monitoring: a review on its application (2009) Mutat. Res., 682, pp. 71-81Ng, C.-T., Li, J.J., Bay, B.-H., Yung, L.-Y.L., Current studies into the genotoxic effects of nanomaterials (2010) J. Nucleic Acids, 2010, pp. 1-12Landsiedel, R., Kapp, M.D., Schulz, M., Wiench, K., Oesch, F., Genotoxicity investigations on nanomaterials: methods, preparation and characterization of test material, potential artifacts and limitations-many questions, some answers (2009) Mutat. Res., 681, pp. 241-258Bolle, P., Mastrangelo, S., Tucci, P., Evandri, M.G., Clastogenicity of atrazine assessed with the Allium cepa test (2004) Environ. Mol. Mutagen., 43, pp. 137-141Srivastava, K., Mishra, K.K., Cytogenetic effects of commercially formulated atrazine on the somatic cells of Allium cepa and Vicia faba (2009) Pestic. Biochem. Physiol., 93, pp. 8-12Manske, M.K., Beltz, L.A., Dhanwada, K.R., Low-level atrazine exposure decreases cell proliferation in human fibroblasts (2004) Arch. Environ. Contam. Toxicol., 46, pp. 438-444Freeman, J.L., Rayburn, A.L., Aquatic herbicides and herbicide contaminants: in vitro cytotoxicity and cell-cycle analysis (2006) Environ. Toxicol., 21, pp. 256-263Gammon, D.W., Aldous, C.N., Carr, W.C., Sanborn, J.R., Pfeifer, K.F., A risk assessment of atrazine use in California: human health and ecological aspects (2005) Pest Manag. Sci., 61, pp. 331-355Cavas, T., In vivo genotoxicity evaluation of atrazine and atrazine-based herbicide on fish Carassius auratus using the micronucleus test and the comet assay (2011) Food Chem. Toxicol., 49, pp. 1431-1435Nwani, C.D., Lakra, W.S., Nagpure, N.S., Kumar, R., Kushwaha, B., Srivastava, S.K., Toxicity of the herbicide atrazine: effects on lipid peroxidation and activities of antioxidant enzymes in the freshwater fish Channa Punctatus (Bloch) (2010) Int. J. Environ. Res. Public Health, 7, pp. 3298-3312