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Synthesis, herbicidal activity and soil degradation of novel 5-substituted sulfonylureas as AHAS inhibitors.
Zhou, Sha; Zhao, Lv-Ting; Meng, Fan-Fei; Hua, Xue-Wen; Li, Yong-Hong; Liu, Bin; Chen, Jie; Chen, An-Liang; Li, Zheng-Ming.
Afiliación
  • Zhou S; Collaborative Innovation Center of Green Pesticide, National Joint Engineering Laboratory of Biopesticide Preparation, Zhejiang A&F University State Key Laboratory of Subtropical Silviculture, College of Forestry and Biotechnology, Zhejiang A & F University, Hangzhou, China.
  • Zhao LT; State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin, China.
  • Meng FF; Collaborative Innovation Center of Green Pesticide, National Joint Engineering Laboratory of Biopesticide Preparation, Zhejiang A&F University State Key Laboratory of Subtropical Silviculture, College of Forestry and Biotechnology, Zhejiang A & F University, Hangzhou, China.
  • Hua XW; State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin, China.
  • Li YH; College of Agriculture, Liaocheng University, Liaocheng, China.
  • Liu B; State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin, China.
  • Chen J; State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin, China.
  • Chen AL; Collaborative Innovation Center of Green Pesticide, National Joint Engineering Laboratory of Biopesticide Preparation, Zhejiang A&F University State Key Laboratory of Subtropical Silviculture, College of Forestry and Biotechnology, Zhejiang A & F University, Hangzhou, China.
  • Li ZM; Collaborative Innovation Center of Green Pesticide, National Joint Engineering Laboratory of Biopesticide Preparation, Zhejiang A&F University State Key Laboratory of Subtropical Silviculture, College of Forestry and Biotechnology, Zhejiang A & F University, Hangzhou, China.
Pest Manag Sci ; 78(12): 5313-5324, 2022 Dec.
Article en En | MEDLINE | ID: mdl-36054636
BACKGROUND: Chlorsulfuron, metsulfuron-methyl and ethametsulfuron can damage sensitive crops in rotation pattern as a result of their long persistence in soil. To explore novel sulfonylurea (SU) herbicides with favorable soil degradation rates, four series of SUs were synthesized through a structure-based drug design (SBDD) strategy. RESULTS: The target compounds, especially Ia, Id and Ie, exhibited prospective herbicidal activity against dicotyledon oil seed rape (Brassica campestris), amaranth (Amaranthus retroflexus), monocotyledon barnyard grass (Echinochloa crusgalli) and crab grass (Digitaria sanguinalis) at a concentration of 15 a.i. g ha-1 . Additionally, Ia, Id and Ig displayed excellent inhibitory effects against AtAHAS, with Kapp i values of 59.1, 34.5 and 71.8 µm, respectively, which were much lower than that of chlorsulfuron at 149.4 µm. The π-π stack and H-bonds between the Ia conformation and AtAHAS in the molecular docking results confirmed the series of compounds to be conventional AHAS inhibitors. In alkaline soil (pH = 8.46), compounds Ia-Ig revealed various degrees of acceleration in the degradation rate compared with chlorsulfuron. Besides, compound Ia showed considerable wheat and corn safety under postemergence at the concentration of 30, 60 and even 120 a.i. g ha-1 . CONCLUSION: Overall, based on the synthetic procedure, herbicidal activity, soil degradation and crop safety, the Ia sulfonylureas series were chosen to be investigated as prospective AHAS inhibitors. The 5-dimethylamino group on SUs accelerated the degradation rate at different levels in alkaline soils which seems to be controllable in conventional cropping systems in their further application. © 2022 Society of Chemical Industry.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Echinochloa / Herbicidas Tipo de estudio: Observational_studies Idioma: En Revista: Pest Manag Sci Asunto de la revista: TOXICOLOGIA Año: 2022 Tipo del documento: Article País de afiliación: China Pais de publicación: Reino Unido
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Echinochloa / Herbicidas Tipo de estudio: Observational_studies Idioma: En Revista: Pest Manag Sci Asunto de la revista: TOXICOLOGIA Año: 2022 Tipo del documento: Article País de afiliación: China Pais de publicación: Reino Unido