Qu, Ren-Yu; Nan, Jia-Xu; Yan, Yao-Chao; Chen, Qiong; Ndikuryayo, Ferdinand; Wei, Xue-Fang; Yang, Wen-Chao; Lin, Hong-Yan; Yang, Guang-Fu published the artcile< Structure-Guided Discovery of Silicon-Containing Subnanomolar Inhibitor of Hydroxyphenylpyruvate Dioxygenase as a Potential Herbicide>, Application of C4H5N3, the main research area is triketonequinazolinedione preparation hydroxyphenylpyruvate dioxygenase inhibitor herbicide; crop safety weed control wheat peanut MBQ derivative; 4-dione; herbicide; hydrophobic interaction; hydroxyphenylpyruvate dioxygenase; lead optimization; quinazoline-2.
4-Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) has been recognized as one of the most promising targets in the field of herbicide innovation considering the severity of weed resistance currently. In a persistent effort to develop effective HPPD-inhibiting herbicides, a structure-guided strategy was carried out to perform the structural optimization for triketone-quinazoline-2,4-diones, a novel HPPD inhibitor scaffold first discovered in our laboratory Herein, starting from the crystal structure of Arabidopsis thaliana (At)HPPD complexed with 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-(o-tolyl)quinazoline-2,4(1H,3H)-dione (MBQ), three subseries of quinazoline-2,4-dione derivatives were designed and prepared by optimizing the hydrophobic interactions between the side chain of the core structure at the R1 position and the hydrophobic pocket at the active site entrance of AtHPPD. 6-(2-Hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-(3-(trimethylsilyl)prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione (I) with the best inhibitory activity against AtHPPD was identified to be the first subnanomolar-range AtHPPD inhibitor (Ki = 0.86 nM), which significantly outperformed that of the lead compound MBQ (Ki = 8.2 nM). Further determination of the crystal structure of AtHPPD in complex with compound 60 (1.85 Å) and the binding energy calculation provided a mol. basis for the understanding of its high efficiency. Addnl., the greenhouse assay indicated that 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-propylquinazoline-2,4(1H,3H)-dione (II) and compound I showed acceptable crop safety against peanut and good herbicidal activity with a broad spectrum. Moreover, compound II also showed superior selectivity for wheat at the dosage of 120 g ai/ha and favorable herbicidal efficacy toward the gramineous weeds at the dosage of as low as 30 g ai/ha. We believe that compounds II and I have promising prospects as new herbicide candidates for wheat and peanut fields.
Journal of Agricultural and Food Chemistry published new progress about Abutilon theophrasti. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Application of C4H5N3.
Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem