Protoporphyrinogen oxidase-inhibiting activity of the new,wheat-selective isoindoldione herbicide,cinidon-ethyl

Cinidon-ethyl (BAS 615H) is a new herbicide of isoindoldione structure which selectively controls a wide spectrum of broadleaf weeds in cereals. The uptake, translocation, metabolism and mode of action of cinidon-ethyl were investigated in Galium aparine L, Solanum nigrum L and the tolerant crop species wheat (Triticum aestivum L). When plants at the second-leaf stage were foliarly treated with cinidon-ethyl equivalent to a field rate of 50 g ha^?1 for 48 h, the light requirement for phytotoxicity and the symptoms of plant damage in the weed species, including rapid chlorophyll bleaching, desiccation and necrosis of the green tissues, were identical to those of inhibitors of porphyrin synthesis, such as acifluorfen-methyl. The selectivity of cinidon-ethyl between wheat and the weed species has been quantified as approximately 500-fold. Cinidon-ethyl strongly inhibited protoporphyrinogen oxidase (Protox) activity in vitro, with I₅₀ values of approximately 1 nM for the enzyme isolated from the weed species and from wheat. However, subsequent effects of herbicide action, with accumulation of protoporphyrin IX, light-dependent formation of 1-aminocyclopropane-1-carboxylic acid-derived ethylene, ethane evolution and desiccation of the green tissue, were induced by cinidon-ethyl only in the weed species. After foliar application of ¹⁴C] cinidon-ethyl, the herbicide, due to its lipophilic nature, was rapidly adsorbed by the epicuticular wax layer of the leaf surface before it penetrated into the leaf tissue more slowly. No significant differences between foliar and root absorption and translocation of the herbicide by S nigrum, G aparine and wheat were found. After foliar or root application of ¹⁴C]- cinidon-ethyl, translocation of ¹⁴C into untreated plant parts was minimal, as demonstrated by combustion analysis and autoradiography. Metabolism of ¹⁴C]cinidon-ethyl via its E-isomer and acid to further metabolites was more rapid in wheat than in S nigrum and G aparine. After 32 h of foliar treatment with 50 g ha^?1 of the ¹⁴C]-herbicide, approximately 47%, 36%, and 12% of the absorbed radioactivity, respectively, were found as unchanged parent or its biologically low active E-isomer and acid in the leaf tissue of G aparine, S nigrum and wheat. In conclusion, cinidon-ethyl is a Protox-inhibiting, peroxidizing herbicide which is effective through contact action in the green tissue of sensitive weed species. It is suggested that a more rapid metabolism, coupled with moderate leaf absorption, contribute to the tolerance of wheat to cinidon-ethyl. © 1999 Society of Chemical Industry