Weeds resistant to the s‐triazine herbicide atrazine also show resistance to the triazinone herbicide metribuzin. However, with highly lipophilic triazinones, thylakoids isolated from atrazine‐resistant Amaranthus retroflexus (mutation at position Ser264 of the photosystem II D‐1 reaction centre protein) in general show a higher pI50 value in photosystem II electron transport than those from the wild type (i.e. negative cross‐resistance; ‘supersensitivity’). A quantitative structure–activity relationship (QSAR) can be established, wherein the lipophilicity of the compound plays a major role. In in‐vivo experiments, it was found that the triazinone DRW2698 killed resistant Amaranthus retroflexus and Chenopodium album whereas the wild type was almost unaffected. Triazinones were further investigated in five different mutants of Chlamydomonas rheinhardtii (mutations in the D‐1 protein at positions Ser264, Ala251, Leu275, Phe255, and Val219). Inhibitory activity of all triazinones was generally enhanced in the Phe255 mutant but decreased in the Val219 mutant. In the other mutants, biological activity was decreased when position 3 of the triazinone was substituted by CH3, OCH3, SCH3, NHCH3 or N(CH3)2. However, negative cross‐resistance was again observed when this position was occupied by free thiol. It is therefore suggested that these two groups of triazinones orient themselves differently within the herbicide binding niche of the photosystem II D‐1 protein.
Summary
inhibitory activities of existing graminicides on root regeneration from monocotyledonous (oat) and dicotyledonous (soybean) plant cuttings in the light, in the dark and on algal growth were compared with the respective inhibitory activities of the new herbicide 2‐(2‐benzothiazo‐lyl‐oxy)‐N‐methyl‐N‐phenylacetamide (mefenacet). The mefenacet activity spectrum resembled that of the α‐chloroacetamide herbicides. Herbicide groups of other structure‐activity can be distinguished by their distinct activity spectrum. The mono‐oxygenase inhibitors piperonyl but‐oxide (PBO) and 1‐aminobenzotriazole (ABT) were found to antagonize the inhibitory activities of herbicides from the thiolcarbamate, α‐chloroacetamide, and oxyacetic acid amide structure groups in the oat rooting and leaf growth tests. The critical evaluation of the presently available information on graminicide and safener mode of action suggests the concept that lipid biosynthesis on the physiological level and mono‐oxygenase type enzymes on the biochemical level may hold the target sites for many of the graminicides and safeners discussed.
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