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Triazolopyrimidines as a New Herbicidal Lead for Combating Weed Resistance Associated with Acetohydroxyacid Synthase Mutation
- Source :
- Journal of Agricultural and Food Chemistry. 64:4845-4857
- Publication Year :
- 2016
- Publisher :
- American Chemical Society (ACS), 2016.
-
Abstract
- Acetohydroxyacid synthase (AHAS; also known as acetolactate synthase; EC 2.2.1.6, formerly EC 4.1.3.18) is the first common enzyme in the biosynthetic pathway leading to the branched-chain amino acids in plants and a wide range of microorganisms. Weed resistance to AHAS-inhibiting herbicides, increasing at an exponential rate, is becoming a global problem and leading to an urgent demand of developing novel compounds against both resistant and wild AHAS. In the present work, a series of novel 2-aroxyl-1,2,4-triazolopyrimidine derivatives (a total of 55) were designed and synthesized with the aim to discover an antiresistant lead compound. Fortunately, the screening results indicated that many of the newly synthesized compounds showed a better, even excellent, inhibition effect against both the wild-type Arabidopsis thaliana AHAS and P197L mutants. Among them, compounds 5-3 to 5-17, compounds 5-19 to 5-26, compounds 5-28 to 5-45, and compound 5-48 have the lower values of resistance factor (RF) and display a potential power to overcome resistance associated with the P197L mutation in the enzyme levels. Further greenhouse in vivo assay showed that compounds 5-15 and 5-20 displayed "moderate" to "good" herbicidal activity against both the wild type-and the resistant (P197L mutation) Descurainia sophia, even at a rate as low as 0.9375 (g of ai/ha). The above results indicated that these two compounds could be used as new leads for the future development of antiresistance herbicides.
- Subjects :
- Models, Molecular
Weed Control
Mutant
Arabidopsis
Plant Weeds
Biology
010402 general chemistry
01 natural sciences
Structure-Activity Relationship
chemistry.chemical_compound
Biosynthesis
Botany
Structure–activity relationship
Arabidopsis thaliana
Enzyme Inhibitors
Plant Proteins
chemistry.chemical_classification
Acetolactate synthase
Herbicides
Triazines
010405 organic chemistry
General Chemistry
biology.organism_classification
0104 chemical sciences
Amino acid
Acetolactate Synthase
Kinetics
Biochemistry
chemistry
Brassicaceae
Mutation
biology.protein
General Agricultural and Biological Sciences
Weed
Lead compound
Herbicide Resistance
Subjects
Details
- ISSN :
- 15205118 and 00218561
- Volume :
- 64
- Database :
- OpenAIRE
- Journal :
- Journal of Agricultural and Food Chemistry
- Accession number :
- edsair.doi.dedup.....d04ef65a3bdb5e9ab9fb5333ed419bbb