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Synthesis and agricultural antimicrobial evaluation of new quinazoline derivatives containing both a piperazine linker and the N-acetyl moiety.
An, Lian; Yang, Lan; Yan, Taisen; Yi, Mingyan; Liu, Songsong; Li, Hong; Bao, Xiaoping.
Afiliación
  • An L; State Key Laboratory of Green Pesticides, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Centre for Research and Development of Fine Chemicals, Guizhou University, Guiyang, People's Republic of China.
  • Yang L; College of Pharmacy, Guizhou University, Guiyang, People's Republic of China.
  • Yan T; State Key Laboratory of Green Pesticides, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Centre for Research and Development of Fine Chemicals, Guizhou University, Guiyang, People's Republic of China.
  • Yi M; State Key Laboratory of Green Pesticides, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Centre for Research and Development of Fine Chemicals, Guizhou University, Guiyang, People's Republic of China.
  • Liu S; State Key Laboratory of Green Pesticides, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Centre for Research and Development of Fine Chemicals, Guizhou University, Guiyang, People's Republic of China.
  • Li H; State Key Laboratory of Green Pesticides, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Centre for Research and Development of Fine Chemicals, Guizhou University, Guiyang, People's Republic of China.
  • Bao X; State Key Laboratory of Green Pesticides, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Centre for Research and Development of Fine Chemicals, Guizhou University, Guiyang, People's Republic of China.
Pest Manag Sci ; 80(10): 5307-5321, 2024 Oct.
Article en En | MEDLINE | ID: mdl-38899477
ABSTRACT

BACKGROUND:

To discover more efficient agricultural antimicrobial agents, a series of new quinazoline derivatives containing both a piperazine linker and the N-acetyl moiety were prepared and assessed for their antibacterial and antifungal activities.

RESULTS:

All the target compounds were characterized by 1H and 13C NMR as well as high-resolution mass spectrometry (HRMS), and the chemical structure of the most potent compound E19 incorporating a 4-trifluoromethoxy substituent was clearly confirmed via single crystal X-ray diffraction measurements. The bioassay results indicated that some compounds possessed notable inhibitory effects in vitro against the bacterium Xanthomonas oryzae pv. oryzicola (Xoc). For example, compound E19 had an EC50 (effective concentration for 50% activity) value of 7.1 µg/mL towards this pathogen, approximately 15- and 10-fold more effective than the commercial bactericides thiodiazole copper and bismerthiazol (EC50 = 110.2 and 72.4 µg/mL, respectively). Subsequently, the mechanistic studies showed that compound E19 likely exerted its antibacterial efficacies by altering the cell morphology, increasing the permeability of bacterial cytoplasmic membrane, suppressing the production of bacterial extracellular polysaccharides and the extracellular enzyme activities (amylase and cellulase), and blocking the swimming motility of Xoc. Moreover, the proteomic analysis revealed that compound E19 could reduce the bacterial flagellar biosynthesis and decrease the flagellar motility by down-regulating the expression of the related differential proteins.

CONCLUSION:

Compound E19 exhibited good potential for further development as a bactericide candidate for control of Xoc. © 2024 Society of Chemical Industry.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Quinazolinas / Xanthomonas / Antibacterianos Idioma: En Revista: Pest Manag Sci Asunto de la revista: TOXICOLOGIA Año: 2024 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Quinazolinas / Xanthomonas / Antibacterianos Idioma: En Revista: Pest Manag Sci Asunto de la revista: TOXICOLOGIA Año: 2024 Tipo del documento: Article Pais de publicación: Reino Unido