Cyflufenamid
The environmental fate of cyflufenamid has been investigated in a number of laboratory studies using [fluorinated phenyl-U-14C] cyflufenamid. An additional study was performed using [cyclopropyl-2, 3-14C] cyflufenamid. Since the only metabolite formed by the degradation of the cyclopropyl moiety in soil was 14CO2, the data available with this radiolabel is considered sufficient. No additional studies were conducted with cyflufenamid labelled in the phenyl acetic acid moiety since phenyl acetic acid is a naturally occurring substance that would not be formed in significant quantities as a result of cyflufenamid degradation compared to natural background concentrations. The selection and positioning of radiolabelling is therefore considered by the Rapportuer to be sufficient to follow the environmental fate and behaviour of cyflufenamid. Results of laboratory aerobic route and rate of degradation studies carried out at ca. 20°C and 40% MWHC were available for 6 soils dosed with cyflufenamid. Results of cyflufenamid degradation in a single soil at 10°C and 40% MWHC were also available. The metabolite N-cyclopropylmethoxy-2,3-difluoro-6-trifluoromethylbenzamidine (149-F) was a major soil metabolite representing up to 34.7% AR at 44 d in the soils studied. The metabolite 2,3-difluoro-6-trifluoromethylbenzamidine (149-F1) was also a major soil metabolite representing up to 22.9% AR at the end of the study (120 d) in the soils studied. A further major soil metabolite was identified as (Z)-N-(α- cyclopropylmethoxyimino-2,3-difluoro-6-trifluoromethylbenzyl)carbamoylacetic acid (149-F11) and represented up to 18.5% AR at 14 d in the soils studied. A fourth metabolite was characterised as it accounted for more than 5% AR in at least two sequential time points and was identified as 2,3-difluoro-6-trifluoromethylbenzamide (149-F6). 149-F6 represented up to 9.0% AR at 90 d in the soils studied. Residues of the cyflufenamid isomer (E)-N-(α-cyclopropylmethoxyimino-2,3- difluoro-6-trifluoromethylbenzyl)-2-phenylacetamide (149-(E)-FB) were detected in all soils at up to 5.7% AR at the end of the study (120 d). The technical grade material was noted to contain the isomer at a maximum concentration of 1.5%. At 120 d 14CO2 represented <0.1% AR in the fluorinated phenyl labelled studies, and represented 49.8% AR at 45 d in the cyclopropyl labelled study. The heavily fluorinated benzene ring is therefore very stable to microbial degradation and the Applicant did not provide any further information to address this issue. At 120 d unextracted radioactivity accounted for up to 36.8% AR (fluorinated phenyl label) or 27.0% AR (cyclopropyl label, 45 d).