The mode of action of RH‐1965: a new phenylpyrimidinone bleaching herbicide

RH‐1965 is a new bleaching herbicide which causes newly developing leaf tissue to emerge devoid of photosynthetic pigments. Mode‐of‐action studies revealed that RH‐1965 inhibited the accumulation of both total chlorophyll and β‐carotene. Concomitantly, it induced the accumulation of the β‐carotene precursors, phytoene, phytofluene and, in particular, ξ‐carotene. Inhibition of chlorophyll accumulation by RH‐1965 is attributed to the photo‐oxidative destruction of chlorophyll in the absence of β‐carotene because RH‐1965 blocked chlorophyll accumulation to a greater extent under high light (50–330 µE m⁻² s⁻¹) than under low light (0.8 µE m⁻² s⁻¹) conditions. Radish (Raphanus sativus L) and barnyardgrass (Echinochloa crus‐galli (L) Beauv) were very senstive to RH‐1965. Under high light (330 µE m⁻² s⁻¹), the I₅₀ values for inhibition of chlorophyll accumulation were 0.10 and 0.15 µM , respectively. Wheat (Triticum aestivus L), on the other hand, was much less sensitive to RH‐1965 (I₅₀ = 1.4 µM ). It is concluded that the mode of action of RH‐1965 involves the inhibition of ξ‐carotene desaturation. © 2000 Society of Chemical Industry     

Mode of action of new diethylamines in lycopene cyclase inhibition and in photosystem II turnover

The new bleaching herbicidal compound N,N‐diethyl‐N‐(2‐undecynyl)amine (NDUA) is identified here as an inhibitor of lycopene cyclase and is compared with the known cyclase inhibitors N,N‐diethyl‐N‐[2‐(4‐chlorophenylthio)ethyl]amine (CPTA) and N,N‐diethyl‐N‐[2‐(4‐methylphenoxy)ethyl]amine (MTPA). HPLC separation of chloroplast pigments shows lycopene accumulation in NDUA treated tissue. Variation in chain length of the undecynylamine moeity of NDUA from 7 to 21 C atoms reveals an optimum of 11 to 14 C atoms for herbicidal activity. A series of seven further analogues of NDUA and CPTA reveals the structural elements necessary for inhibition of lycopene cyclase. The effect of NDUA derivatives on photosynthesis has been studied in Chlamydomonas reinhardtii. Photosynthesis is highly sensitive, particularly towards the C14 and longer chain length analogues at nanomolar concentrations. It is shown that the breakdown of photosynthesis by NDUA is due to interference with the turnover of the D1 protein of the photosystem II reaction centre that requires the continous biosynthesis of the two reaction‐centre β‐carotene moieties in the reassembly phase. The D1 protein disappearance is most marked under strong light conditions. The depletion of photosystem II occurs before total pigment bleaching. This newly recognized mechanism in herbicidal activity is also the basis for the mode of action of other lycopene cyclase inhibitors as well as phytoene desaturase inhibitors. © 2001 Society of Chemical Industry