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Tebuconazole

Overview
 
CAS Number: 107534-96-3
Synonyms: Ethyltrianol,  Etiltrianol,  Fenetrazole,  Terbuconazole,  Terbutrazole, (+/-)-alpha-(2-(4-chlorophenyl)ethyl)-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazol-1-ethanol , 1-(4-Chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazole-1-yl-methyl)pentane-3-ol, 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-ylmethyl)-3-pentanol, 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-ylmethyl)pentan-3-ol, 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazolylmethyl)pentan-3-ol, 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)-3-pentanol, 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol, 1-(4-chlorphenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)-3-pentanol, 1-(4-chlorphenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol, 1H-1,2,4-triazole-1-ethanol, a-[2-(4-chlorophenyl)ethyl]-a-(1,1-dimethylethyl)-, 1H-1,2,4-triazole-1-ethanol, a-[2-(4-chlorophenyl)ethyl]-a-(1,1-dimethylethyl)-, ()-, Bay HWG 1680, Elite, Folicur, Folicur 1.2 EC , GWG 1609 , HWG 1608, Lynx 1.2 , Preventol A 8, Raxil, a-(2-(4-chlorophenyl)ethyl)-a-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol
Contaminant Type: Chemical

Tebuconazole is a synthetic triazole fungicide effective against various smut and bunt diseases in cereals and other field crops [2152], and commonly used on peppers [2145]. It is widely used as a biocide in various products for material protection e.g. treatment of wood, concrete, paints and roofs [2143]. Its IUPAC name is (RS)-1-p-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazole-1-ylmethyl)pentan-3-ol [2148].

Tebuconazole is not regulated by USEPA in drinking water. However, it is regulated by the European Union (EU) under the EU Drinking Water Directive (98/83/EC) which requires pesticide concentrations in drinking water not exceed 0.1 μg/L for a single pesticide and 0.5 μg/L for total pesticides [2146].

Tebuconazole is often supplied as an oil in water emulsion or concentrate that is mixed with water and used as a spray [2152]. Similar to a great number of pesticides, tebuconazole is bio-recalcitrant and non-biodegradable [2146]. It is resistant to chemical and/or photochemical degradation under typical environmental conditions [2111]. It is non-volatile with a very low Henry's Law constant. Lab and field soil degradation studies found tebuconazole to be moderately to very persistent in soil (lab studies DT50>365 days, field studies DT50 range 19.9 to 91.6 days). Its key metabolite is 1,2,4-triazole which is formed in the soil. Its solubility in water is low, 36 mg/L at 20°C [2152]. The primary pathway for tebuconazole to enter water courses is through surface runoff and spray drift [2144].

Azole fungicides including tebuconazole may have the potential to affect the endocrine system of aquatic organisms. Their biological activity is based on the inhibition of certain pathways of steroidogenesis [2144]. In humans, it is known to impact the liver/blood system [2152]. 

Date of Literature Search: April 2012.



2111 Burrows, H., Canle, M., Sataballa, J. and Steenken, S. ; 2002; Reaction pathways and mechanisms of photodegradation of pesticides; Journal of Photochemistry and Photobiology B: Biology; 67:70
2143 Stamatis, N., Hela, D. and Konstantinou, I.; 2010; Occurrence and removal of fungicides in municipal sewage treatment plant ; J. Hazardous Materials; 175:1-3:829
2144 Kahle, M., Buerge, I., Hauser, A., Muller, M. and Poiger, T.; 2008; Azole Fungicides: Occurrence and Fate in Wastewater and Surface Waters; Environ. Sci. Technol. ; 42:19:7193
2145 Navarro, S., Fenoll, J., Vela, N., Ruiz, E. and Navarro, G.; 2011; Removal of ten pesticides from leaching water at pilot plant scale by photo-Fenton treatment; Chemical Engineering Journal; 167:1:42
2146 Navarro, S., Fenoll, J., Vela, N., Ruiz, E. and Navarro, G.; 2009; Photocatalytic degradation of eight pesticides in leaching water by use of ZnO under natural sunlight; J. Hazardous Materials; 172:2-3:1303
2148 FAO/WHO; 1994; Pesticide residues in food - 1994. Report of the Joint Meeting of the FAO Panel of Experts on Pesticides Residues in Food and the Environment and the WHO Expert Group on Pesticide Residues; Pesticide residues in food - 1994. Report of the Joint Meeting of the FAO Panel of Experts on Pesticides Residues in Food and the Environment and the WHO Expert Group on Pesticide Residues ; FAO Plant Production and Protection Paper 127. pp. 1055-1096, Rome, 1995
2152 Agricuture & Environment Reserach Unit, Univeristy of Hertfordshire; 2012; PPDB: Pesticide Properties Database; http://sitem.herts.ac.uk/aeru/; As posted on April 18, 2012, Agricuture & Environment Reserach Unit, University of Hertfordshire, Hatfield, Herfordshire, United Kingdom



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