Discovery of flufenoxystrobin: Novel fluorine-containing strobilurin fungicide and acaricide

In a continuous study on the high-value-added exploration of a renewable forest bioresource turpentine in modern organic agriculture, two series of α-pinene derivatives containing amide and α,β-unsaturated ketone pharmacophores were prepared. Through an in-depth fungicidal activity study, the title compounds presented excellent inhibitory activity against common crop fungi, especially Sclerotinia sclerotiorum, and the notable EC50 values of α,β-unsaturated compounds 3u (funan containing) and 3v (thiophene containing) were 1.657 and 1.749 μg/mL, respectively. Further physiological and biochemical studies on S. sclerotiorum revealed that compounds 3u and 3v reduced the ergosterol content in the cell membrane and increased the permeability of the cell membrane. In combination with their effect on mycelial morphology, the title compounds might have inhibitory effects on the biosynthesis of ergosterol, which is a paramount component of the target cell membrane. Moreover, quantitative structure–activity relationship (QSAR) and SAR studies revealed that the charge distribution of α,β-unsaturated carbonyl ketone derivatives played an important role in the observed fungicidal activity. In summary, this study highlights the design and development of novel high-efficacy turpentine-based antifungal agents.

Section: ■ Results and Discussionmentioning

confidence: 99%

Taking Advantage of the Renewable Forest Bioresource Turpentine to Prepare α,β-Unsaturated Compounds as Highly Efficient Fungicidal Candidates

Pan

Geng

Jiang

et al. 2021

“…Fluorine-containing compound 30 exhibited excellent fungicidal activities against E. graminis with 85% control at 0.39 μg/mL, which was much better than azoxystrobin (30%) and pyraclostrobin (70%). Field trials showed that the fungicidal activities of compound 30 were almost equivalent to those of pyraclostrobin, higher than those of triadimefon . The essential oil-based strobilurin 31 showed remarkable in vitro inhibitory activities against S. sclerotiorum , Pestalotiopsis theae , Magnaporthe grisea , and Phomopsis adianticola with EC 50 values of 0.003, 0.04, 0.95, and 3.06 μg/mL, respectively, which were superior to those of azoxystrobin (EC 50 = 18.75, 2.54, 2.41, and 35.3 mg/L, respectively) .…”

Section: β-Methoxyacrylate Derivatives As Pesticidesmentioning

confidence: 99%

Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc₁ Inhibitors for Novel Pesticide Discovery

Luo

Ning

Rao

2022

β-Methoxyacrylate derivatives represent a new class of pesticides, which have attracted increasing attention owing to their unique structure, broad biological activity, and unique mechanisms of action. They inhibit mitochondrial respiration via preventing electron transfer at the Qo site of the cytochrome bc 1 complex and thus are identified as cyt bc 1 inhibitors. A variety of βmethoxyacrylate derivatives have been reported by many research groups for discovery of novel pesticides with improved expected activities. This review focuses on development of β-methoxyacrylate derivatives with great significance as pesticides such as fungicides, acaricides, insecticides, herbicides, and antiviral agents. In addition, the structure−activity relationships (SARs) of βmethoxyacrylate derivatives are summarized. Moreover, the cause of resistance to β-methoxyacrylate fungicides and some solutions are also introduced. Finally, the development trend of β-methoxyacrylate derivatives as pesticides is explored. We hope the review will give a guide to develop novel β-methoxyacrylate pesticides in the future.

“…In 2016, Li and co-workers introduced the substructure of strobilurin via benzyl ether to yield compound 34 (Figure ), which had an excellent fungicidal activity of 80–90% against Erysiphe graminis at a concentration of 1.56 mg/L and was better than azoxystrobin (60%) and kresoxim-methyl (40%). Zhang and co-workers demonstrated that the introduction of a −F or −CF 3 group to the pyridine ring could improve its antifungal activity and expand the antifungal spectrum, which is helpful to the development of novel antifungal agrichemicals.…”

Section: Biological Activities Of Tfmp Derivativesmentioning

confidence: 99%

Trifluoromethylpyridine: An Important Active Fragment for the Discovery of New Pesticides

Zheng

Dai

Jin

et al. 2022

Trifluoromethylpyridine (TFMP) is a biologically active fragment formed by connecting trifluoromethyl and pyridine ring. As a result of its unique physical and chemical properties and outstanding biological activity, a variety of pesticide compounds with the TFMP fragment have been discovered and marketed and have played important roles in crop protection research. It is therefore a timely and valuable task to summarize the rationality on how to create new molecules containing TFMP fragments based on the structure–activity relationships, design mentality, and potential mechanism. This review gives a brief summary on the pesticides containing TFMP fragments in the past 5 years and introduces the latest progress of our group in this field. The aim is to provide readers with a convenient route to touch this topic and hopefully serve some educational purpose for graduate students as well.