Hostname: page-component-cd9895bd7-jn8rn Total loading time: 0 Render date: 2024-12-27T03:14:45.989Z Has data issue: false hasContentIssue false

Comparative Phytotoxicity Assays of the Herbicide Alloxydim and Its Main Identified Photoproduct in Cereal and Broadleaves Crops

Published online by Cambridge University Press:  20 January 2017

Pilar Sandín-España*
Affiliation:
DTEVPF—Unit of Plant Protection Products, INIA, Madrid, 28040
Beatriz Sevilla-Morán
Affiliation:
DTEVPF—Unit of Plant Protection Products, INIA, Madrid, 28040
Mercedes Villarroya-Ferruz
Affiliation:
DTEVPF—Unit of Plant Protection Products, INIA, Madrid, 28040
José L. Alonso-Prados
Affiliation:
DTEVPF—Unit of Plant Protection Products, INIA, Madrid, 28040
M. Inés Santín-Montanyá
Affiliation:
Department of Plant Protection, INIA, Madrid, 28040
*
Corresponding author's E-mail: [email protected]

Abstract

When herbicides are sprayed in the field, a proportion of the herbicide falls onto leaves and soil surfaces, where it can be exposed to sunlight, generating photoproducts that can be more toxic and/or persistent than the parent substance and affect human health and the environment. The aim of this study was to identify the photoproducts of the herbicide alloxydim in leaf and soil model systems and to perform phytotoxicity studies. Alloxydim was rapidly photodegraded in systems simulating plant cuticles and soil surfaces, with half-lives ranging from 1 to 30 min. The main by-product, identified by LC-Qtof-MS as deallyoxylated alloxydim, was more stable than the active substance. The EC50 values on root lengths of different varieties of wheat plants and one grass weed ranged from 0.38 to 0.50 mg L−1 for alloxydim. In contrast, the EC50 values for deallyoxylated alloxydim ranged from 94 to 600 mg L−1 in the same species and in crops where the herbicide was applied. Special attention should be given to alloxydim degradation products because of the rapid degradation of this herbicide. Comparative bioassay studies between alloxydim and its photostable by-product showed that the by-product presents low phytotoxicity, whereas alloxydim can cause injury to neighboring and succeeding cereal crops.

Type
Physiology/Chemistry/Biochemistry
Copyright
Copyright © Weed Science Society of America 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Literature Cited

Boxall, ABA, Sinclair, CI, Fenner, K, Kolpin, DW, Maund, SJ (2004) When synthetic chemicals degrade in the environment. Environ Sci Technol. 38:368A375A Google Scholar
Campbell, JR, Penner, D (1985) Abiotic transformations of sethoxydim. Weed Sci. 33:435439 CrossRefGoogle Scholar
Falb, LN, Bridges, DC, Smith, AE (1990) Effects of pH and adjuvants on clethodim photodegradation. J Agric Food Chem. 38:875878 Google Scholar
Hashimoto, Y, Ishihara, K, Soeda, Y (1979a) Fate of alloxydim–sodium on or in soybean plants. J Pestic Sci. 4:299304 CrossRefGoogle Scholar
Hashimoto, Y, Ishihara, K, Soeda, Y (1979b) Nature of the residue in soybean plant after treatment of alloxydim–sodium. J Pestic Sci. 4:375378 Google Scholar
Iwataki, I, Hirono, Y (1979) The chemical structure and herbicidal activity of alloxydim–sodium and related compounds. Pages 235243 in Geissbühler, H, Brooks, GT, Kearney, PC, eds. Advances in Pesticide Science. Oxford, UK Pergamon Press Google Scholar
Kapanen, A, Itavaara, M (2001) Ecotoxicity tests for compost applications. Ecotox Environ Safe. 49:16 Google Scholar
Mahmoud, WMM, Toolaram, AP, Menz, J, Leder, C, Schneider, M, Küemmerer, K (2014) Identification of phototransformation products of thalidomide and mixture toxicity assessment: an experimental and quantitative structural activity relationships (QSAR) approach. Water Res. 49:1122 CrossRefGoogle ScholarPubMed
Monadjemi, S, Ter Halle, A, Richard, C (2012) Reactivity of cycloxydim toward singlet oxygen in solution and on wax film. Chemosphere. 89:269273 Google Scholar
Ono, S, Shiotani, H, Ishihara, K, Tokieda, M, Soeda, Y (1984) Degradation of the herbicide alloxydim–sodium in soil. J Pestic Sci. 9:471480 CrossRefGoogle Scholar
Sandín-España, P, Llanos, S, Magrans, JO, Alonso-Prados, JL, García-Baudín, JM (2003) Optimization of hydroponic bioassay for herbicide tepraloxydim by using water free from chlorine. Weed Res. 43:451457 CrossRefGoogle Scholar
Sandín-España, P, Sevilla-Morán, B (2012) Pesticide degradation in water. Pages 79130 in Rathore, HS, Nollet, LML, eds. Pesticides: Evaluation of Environmental Pollution. Boca Raton, FL CRC Press Google Scholar
Sandín-España, P, Sevilla-Morán, B, Alonso-Prados, JL, Santín-Montanya, I (2012) Chemical behaviour and herbicidal activity of cyclohexanedione oxime herbicides. Pages 75102 in Naguib, M, Hasaneen, AEG, eds. Herbicides—Properties, Synthesis and Control of Weeds. Rijeka, Croatia InTech Google Scholar
Sandín-España, P, Sevilla-Morán, B, Calvo, L, Mateo-Miranda, M, Alonso-Prados, JL (2013a) Photochemical behavior of alloxydim herbicide in environmental waters. Structural elucidation and toxicity of degradation products. Microchem J. 106:212219 Google Scholar
Sandín-España, P, Sevilla-Morán, B, Villarroya-Ferruz, M, Alonso-Prados, JL, Santín-Montanyá, I (2013b) Photolysis experiments on alloxydim herbicide and biological response of its transformation product. Pages 151174 in Kobayashi, D, Watanabe, E, eds. Handbook on Herbicides: Biological Activity, Classification and Health & Environmental Implications. New York Nova Science Publishers Google Scholar
Santín-Montanya, I, Sandín-España, P, García Baudín, JM, Coll-Morales, J (2007) Optimal growth of Dunaliella primolecta in axenic conditions to assay herbicides. Chemosphere. 66:13151322 Google Scholar
Schippers, N, Schwack, W (2008) Photochemistry of imidacloprid in model systems. J Agric Food Chem. 56:80238029 Google Scholar
Schynowski, F, Schwack, W (1996) Photochemistry of parathion on plant surfaces: relationship between photodecomposition and iodine number of the plant cuticle. Chemosphere. 33:22552562 Google Scholar
Scrano, L, Bufo, SA, D'Auria, M, Meallier, P, Behechti, A, Shramm, KW (2002) Photochemistry and photoinduced toxicity of acifluorfen, a diphenyl-ether herbicide. J Environ Qual. 31:268274 Google Scholar
Seefeldt, SS, Jensen, JE, Patrick Fuerst, E (1995) Log-logistic analysis of herbicide dose–response relationships. Weed Technol. 9:218225 CrossRefGoogle Scholar
Sevilla-Morán, B, Alonso-Prados, JL, García-Baudín, JM, Sandín-España, P (2010) Indirect photodegradation of clethodim in aqueous media. By-product identification by quadrupole time-of-flight mass spectrometry. J Agric Food Chem. 58:30683076 Google Scholar
Sevilla-Morán, B, Sandín-España, P, Vicente-Arana, MJ, Alonso-Prados, JL, García-Baudín, JM (2008) Study of alloxydim photodegradation in the presence of natural substances: elucidation of transformation products. J Photochem Photobiol A. 198:162168 Google Scholar
Shoaf, AR, Carlson, WC (1992) Stability of sethoxydim and its degradation products in solution, in soil, and on surfaces. Weed Sci. 40:384389 Google Scholar
Smith, MC, Shaw, DR, Miller, DK (2005) In-field bioassay to investigate the persistence of imazaquin and pyrithiobac. Weed Sci. 53:121129 Google Scholar
Soeda, Y, Ishihara, K, Iwataki, I, Kamimura, H (1979) Fate of a herbicide 14C-alloxydim-sodium in sugar beets. J Pestic Sci. 4:121128 CrossRefGoogle Scholar
Stoklosa, A, Matraszek, R, Isman, MB, Upadhyaya, MK (2012) Phytotoxic activity of clove oil, its constituents, and its modification by light intensity in broccoli and common lambsquarters (Chenopodium album). Weed Sci. 60:607611 Google Scholar
Swanson, MB, Ivancic, WA, Saxena, AM, Allton, JD, O'Brien, GK, Suzuki, T, Nishizawa, H, Nokata, M (1995) Direct photolysis of fenpyroximate in a buffered aqueous solution under a xenon lamp. J Agric Food Chem. 43:513518 CrossRefGoogle Scholar
Veerasekaran, P, Catchpole, AH (1982) Studies on the selectivity of alloxydim–sodium in plants. Pestic Sci. 13:452–62Google Scholar
Villaverde, JJ, Sevilla-Morán, B, Sandín-España, P, López-Goti, C, Alonso-Prados, JL (2014) Biopesticides in the framework of the European Pesticide Regulation (EC) No. 1107/2009. Pest Manag Sci. 70:25 Google Scholar
Wayne, CE, Wayne, RP (1996) Photochemistry. Oxford, UK Oxford University Press. 98 pCrossRefGoogle Scholar