Discovery of (2-benzoylethen-1-ol)-containing 1,2-benzothiazine derivatives as novel 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibiting-based herbicide lead compounds |
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| Affiliation: | 1. State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, China;2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China;3. College of Resources and Environmental Sciences, China Agricultural University, Beijing, China;1. Jagiellonian University Medical College, Faculty of Pharmacy, Department of Technology and Biotechnology of Drugs, Medyczna 9, 30-688 Kraków, Poland;2. Institute of Pharmaceutical and Medicinal Chemistry, Heinrich-Heine-University, Universitaetsstr. 1, 40225 Duesseldorf, Germany;3. Institute of General and Ecological Chemistry, Technical University of Łódź, Żeromskiego 116 Str., 90-924 Łódź, Poland;1. Department of Pharmacy—Center for Drug Research, Pharmaceutical Biology, University of Munich, Butenandtstrasse 5-13, 81377 Munich, Germany;2. Institute of Pharmaceutical Sciences, ETH Zurich, Vladimir-Prelog-Weg 4, 8093 Zurich, Switzerland;1. Department of Industrial Chemistry “Toso Montanari”, School of Science University of Bologna, viale del Risorgimento 4, 40136 Bologna, Italy;2. Chimie ParisTech—École Nationale Supérieure de Chimie de Paris, 11, rue Pierre et Marie Curie, Paris Cedex 05 75231, France;1. Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Boulevard, Tucson, AZ 85721, USA;2. Department of Pharmacology, University of Arizona, Tucson, AZ 85721, USA |
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| Abstract: | A series of (2-benzoylethen-1-ol)-containing benzothiazine derivatives was synthesized, and their herbicidal activities were first evaluated. The bioassay results indicated that some of 3-benzoyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-1,1-dioxide derivatives displayed good herbicidal activity in greenhouse testing, especially, compound 4w had good pre-emergent herbicidal activities against Brassica campestris, Amaranthus retroflexus and Echinochloa crusgalli even at a dosage of 187.5 g ha−1. More importantly, compound 4w displayed significant inhibitory activity against Arabidopsis thaliana HPPD and was identified as the most potent candidate with IC50 value of 0.48 μM, which is better than the commercial herbicide sulctrione (IC50 = 0.53 μM) and comparable with the commercial herbicide mesotrione (IC50 = 0.25 μM). The structure–activity relationships was studied and provided some useful information for improving herbicidal activity. The present work indicated that (2-benzoylethen-1-ol)-containing 1,2-benzothiazine motif could be a potential lead structure for further development of novel HPPD inhibiting-based herbicides. |
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| Keywords: | Synthesis Benzothiazine Herbicide activity 4-Hydroxyphenylpyruvate dioxygenase Structure–activity relationships |
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