Photodegradation of the pyrethroid insecticide fenpropathrin in water,on soil and on plant foliage

The photodegradation of fenpropathrin [(RS)-α-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate] ( I ), in water, on soil and on plant foliage, was investigated using ¹⁴C-preparations labelled separately at the cyano group, cyclopropyl-C₁ or in the benzyl ring. On exposure to sunlight, I was photodecomposed with initial half-lives of >6 weeks in distilled water, 6.0 weeks in humic acid aqueous solution, 2.7 weeks in river water, 1.6 weeks in sea water and 0.5 of a day in 2% aqueous acetone. A triplet photosensitiser, acetone, together with naturally occurring substances in river and sea water, including humic acid, enhanced the photodegradation of I . On three kinds of soil, I was rapidly photodegraded with initial half-lives of 1–5 days, whereas it was fairly photostable on a mandarin orange leaf. The photoreactions involved were: decarboxylation, hydration of the cyano group to carboxamide, cleavage of the ester or the diphenyl ether linkage, hydrolysis of the carboxamide group to carboxyl, and hydroxylation at either or both of the gem dimethyl groups. The predominant reactions in water were decarboxylation, ester bond cleavage and photo-induced evolution of [¹⁴C] carbon dioxide from the [¹⁴C] cyano label; on soil, hydration or ester bond cleavage predominated. The hydration was also of importance in river and sea water. Decarboxylation did not occur on soil and plant foliage.