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Design, Synthesis, and SAR of Novel 1,3-Disubstituted Imidazolidine or Hexahydropyrimidine Derivatives as Herbicide Safeners
- Source :
- Journal of Agricultural and Food Chemistry. 69:45-54
- Publication Year :
- 2020
- Publisher :
- American Chemical Society (ACS), 2020.
-
Abstract
- Herbicide safeners enhance herbicide detoxification in crops without reducing their herbicidal efficacy against target weeds. To alleviate maize injury caused by the sulfonylurea herbicide nicosulfuron, a series of 1,3-disubstituted imidazolidine or hexahydropyrimidine derivatives were rationally designed via bioisosterism and active subunit combinations. Thirty novel compounds were synthesized using an efficient one-pot method and low-cost raw materials and characterized by IR, 1H NMR, 13C NMR, and high-resolution mass spectrometer (HRMS). Bioactivity and structure-activity relationship (SAR) were evaluated for herbicide safeners tested against nicosulfuron injury. Most of the compounds effectively protected sensitive maize against nicosulfuron damage. The parent skeletons and substituents of the target compounds both substantially influenced their safener activity. Compound I-3 exhibited superior bioactivity compared to the safener isoxadifen-ethyl. Molecular docking simulations disclosed that compound I-3 competed with nicosulfuron for the acetolactate synthase active site and demonstrated that this is the protective mechanism of safeners. The target compound I-3 presented with strong herbicide safener activity in maize and is, therefore, a potential candidate for the development of a novel herbicide safener.
- Subjects :
- 0106 biological sciences
Pyridines
medicine.drug_class
Imidazolidines
Protective Agents
Zea mays
01 natural sciences
Structure-Activity Relationship
chemistry.chemical_compound
Imidazolidine
medicine
Plant Proteins
Acetolactate synthase
biology
Herbicides
Chemistry
010401 analytical chemistry
Rational design
Active site
General Chemistry
Carbon-13 NMR
Sulfonylurea
Combinatorial chemistry
0104 chemical sciences
Molecular Docking Simulation
Acetolactate Synthase
Pyrimidines
Sulfonylurea Compounds
Drug Design
Herbicide safener
biology.protein
Proton NMR
General Agricultural and Biological Sciences
010606 plant biology & botany
Subjects
Details
- ISSN :
- 15205118 and 00218561
- Volume :
- 69
- Database :
- OpenAIRE
- Journal :
- Journal of Agricultural and Food Chemistry
- Accession number :
- edsair.doi.dedup.....43de7d6b6cfed3405f135ab5a9f1c4d6