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Synthesis, Herbicidal Activity, and QSAR of Novel N‑Benzothiazolyl- pyrimidine-2,4-diones as Protoporphyrinogen Oxidase Inhibitors

Zuo, Yang ; Wu, Qiongyou ; Su, Sun-wen ; Niu, Cong-wei ; Xi, Zhen ; Yang, Guang-Fu

Journal of agricultural and food chemistry, 2016-01, Vol.64 (3), p.552-562 [Periódico revisado por pares]

United States: American Chemical Society

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Título:
Synthesis, Herbicidal Activity, and QSAR of Novel N‑Benzothiazolyl- pyrimidine-2,4-diones as Protoporphyrinogen Oxidase Inhibitors
Autor: Zuo, Yang ; Wu, Qiongyou ; Su, Sun-wen ; Niu, Cong-wei ; Xi, Zhen ; Yang, Guang-Fu
Assuntos: Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Herbicides - chemical synthesis ; Herbicides - chemistry ; Herbicides - pharmacology ; Kinetics ; Nicotiana - drug effects ; Nicotiana - enzymology ; Plant Proteins - chemistry ; Plant Proteins - metabolism ; Protoporphyrinogen Oxidase - chemistry ; Protoporphyrinogen Oxidase - metabolism ; Pyrimidinones - chemistry ; Pyrimidinones - pharmacology ; Quantitative Structure-Activity Relationship ; Sulfonamides - chemistry ; Sulfonamides - pharmacology ; Triazoles - chemistry ; Triazoles - pharmacology
É parte de: Journal of agricultural and food chemistry, 2016-01, Vol.64 (3), p.552-562
Descrição: Protoporphyrinogen oxidase (PPO, E.C. 1.3.3.4) is known as a key action target for several structurally diverse herbicides. As a continuation of our research work on the development of new PPO-inhibiting herbicides, a series of novel 3-(2′-halo-5′-substituted-benzothiazol-1′-yl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-diones 9 were designed and synthesized. The bioassay results indicated that a number of the newly synthesized compounds exhibited higher inhibition activity against tobacco PPO (mtPPO) than the controls, saflufenacil and sulfentrazone. Compound 9F-5 was identified as the most potent inhibitor with a K i value of 0.0072 μM against mtPPO, showing about 4.2-fold and 1.4-fold higher potency than sulfentrazone (K i = 0.03 μM) and saflufenacil (K i = 0.01 μM), respectively. An additional green house assay demonstrated that compound 9F-6 (K i = 0.012 μM) displayed the most promising postemergence herbicidal activity with a broad spectrum even at a concentration as low as 37.5 g of active ingredient (ai)/ha. Maize exhibits relative tolerance against compound 9F-6 at the dosage of 150 g ai/ha, but it is susceptible to saflufenacil even at 75 g ai/ha. Thus, compound 9F-6 exhibits the potential to be a new herbicide for weed control in maize fields.
Editor: United States: American Chemical Society
Idioma: Inglês

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Synthesis, Herbicidal Activity, and QSAR of Novel N‑Benzothiazolyl- pyrimidine-2,4-diones as Protoporphyrinogen Oxidase Inhibitors

Zuo, Yang ; Wu, Qiongyou ; Su, Sun-wen ; Niu, Cong-wei ; Xi, Zhen ; Yang, Guang-Fu

United States: American Chemical Society

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