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EC number: 212-634-7 | CAS number: 834-12-8
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Phototransformation in water
Administrative data
Link to relevant study record(s)
Description of key information
Studies have shown ametryn to be susceptible to photolysis in solution under artificial sunlight throughout the environmentally relevant range of pH 5 to pH 9, with a half-life in the region of 20 to 29 hours (1.7 to 2.4 12-hour days), and also under natural sunlight at pH 7 with a half-life in the region of 2544 hours (212 12-hour days).
Key value for chemical safety assessment
Additional information
Three studies are available that describe the phototransformation of the substance.
The key study is a Klimisch-1, GLP-compliant study, sponsored by Sipcam Agro S.A. and carried out in 2002 by Bioagri (Prata Cione AP) in accordance with a method equivalent or similar to OECD 316 (Phototransformation of Chemicals in Water - Direct Photolysis), 2008; no EC method. The objective of the study was to determine the half-life and photolysis rate of Ametryn in aqueous solution by artificial sunlight and to quantify and identify the degradation products. Solutions of Ametryn (ca. 22 mg/L) at pH 5, 7 and 9 were exposed to artificial sunlight from a Xenon lamp (250 W/m2) for 23.8 hours at ca. 25°C. Periodic samples were taken, in which the Ametryn and degradation products were quantified using HPLC, and identified using LC-MS. The results showed Ametryn to be unstable under artificial sunlight, with a half-life estimated to be 23.4 hours at pH 5, 20 hours at pH 7 and 23 hours at pH 9. Only a single degradation product was seen, which mass balance consistently showed to account for ca. 100% of lost test substance, and which was identified as EITD, the des(methylthio) analogue of Ametryn. Ametryn was stable in the dark controls.
The first supporting phototransformation study is a Klimisch-1, GLP-compliant, sponsored by Ciba-Geigy and carried out in 1989 by Agrisearch Incorporated (Spare WC) in accordance with EPA Guidelines, Subdivision N, 163-2 (Photodegradation studies in water). A solution of Ametryn (ca. 10 mg/L) at pH 7 was exposed to natural sunlight at ambient temperatures (5°C to 29°C) for 30 consecutive days. Periodic samples were taken and analysed for 14C-Ametryn and degradation products by TLC. The results showed Ametryn to photolyse slowly under the conditions of the test, with a half-life estimated to be 212 days (12 hours light each, i.e. 2544 hours) and a rate constant of 3.3E-3 per day. Four degradation products were identified, namely the des(methylthio) analogue (GS-32083), the desethyl analogue (GS-11354), the desisopropyl analogue (GS-11355) and the desethyl-des(methylthio) analogue (GS-28304), although each individual degradation product represented less than 5% of the total radiocarbon.
The second supporting phototransformation study is also a Klimisch-1, GLP-compliant, sponsored by Ciba-Geigy and carried out in 1989 by Agrisearch Incorporated (Spare WC) in accordance with EPA Guidlines, Subdivision N, 163-2 (Photodegradation studies in water). A solution of Ametryn (ca. 10 mg/L) at pH 7 was exposed to artificial sunlight from a mercury arc lamp (3.6 to 4.7E-5 W/cm2 – ca. twice the intensity of bright natural sunlight) for 48 hours at ca. 25°C. The results showed Ametryn to photolyse under the conditions of the test, with a half-life estimated to be ca. 29 hours (2.4 12-hour days) and a rate constant of 2.4E-2 per hour. Several degradation products were isolated and characterized by TLC, with the primary degradation product being the des(methylthio) analogue (GS-32083), which represented ca. 35% of the initial radiocarbon dose at 48 hours. Additional products were the desethyl-des(methylthio) analogue (GS-28304, 7% of dose), the desethyl analogue (GS-11354, 5%), GS-17794 (no structure provided, 5%) and the 6-hydroxy analogue (GS-34048, 15%). This author concluded that solution photolysis may be an environmentally relevant transformation process for Ametryn.
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