Synthesis and Evaluation of Essential Oil-Derived β-Methoxyacrylate Derivatives as High Potential Fungicides

Abstract

Essential oils (EOs) are plant-derived aroma compounds with a wide range of biological activity, but their actions are slow, and they are typically unstable to light or heat, difficult to extract and so on. To find highly potential fungicides derived from natural EOs, a series of essential oil-based β-methoxyacrylate derivatives have been designed and synthesized. The target compounds have been screened for their potential fungicidal activity against eleven species of plant pathogen fungi, including Alternaria alternata, Phomopsis adianticola, Pestalotiopsis theae, Sclerotinia sclerotiorum, etc. Compared with intermediates I, the parent essential oils and azoxystrobin, almost all of essential oil-based β-methoxyacrylate derivatives exhibited significantly better fungicidal activity. Further investigation revealed that some compounds showed remarkable inhibitory activities against Pestalotiopsis theae, Phomopsis adianticola, Sclerotinia sclerotiorum and Magnapothe grisea at different concentrations in contrast to the commercial product azoxystrobin. Compound II-8 exhibited particularly significant fungicidal activity.

Antitumor, Antiviral, and Anti-Inflammatory Efficacy of Essential Oils from Atractylodes macrocephala Koidz. Produced with Different Processing Methods

“…Previous literature studies have shown that frying with bran can reduce the dryness of the drug and improve its spleen tonifying activity [49]. EOs are plant-derived aromatic compounds that have a wide range of biological activities, but they act slowly, and they are usually unstable under light or heat, difficult to extract, and so on [50]. Based on this, we used GC/MS to study the EOs components of CA and BA.…”

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

“…Compound 70 , containing a pyrrolidine-2,4-dione moiety, exhibited moderate fungicidal activity against B. cinerea , R. solani , and Fusarium graminearum at 100 μg/mL, still better than that of tenuazonic acid . Compound 71 bearing a carbazole side chain displayed outstanding activity against S. sclerotiorum with IC 50 value of 0.43 μg/mL, close to that of pyraclostrobin (0.15 μg/mL) . Compound 72 possessing an aryloxypyridine as side chain exhibited remarkable activity against S. sclerotiorum with EC 50 value of 0.08 μg/mL, 10-fold more potent than that of azoxystrobin (EC 50 = 0.79 μg/mL) …”

“…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) . Compound 32 , possessing a biphenyl group as side chain, displayed significant activities against B. cinerea with IC 50 value of 0.57 μg/mL, close to that of pyraclostrobin (IC 50 = 0.18 μg/mL).…”

New β-Lactone with Tea Pathogenic Fungus Inhibitory Effect from Marine-Derived Fungus MCCC3A00957

“…Essential oil-based β-methoxyacrylate derivatives have been synthesized and showed remarkable inhibitory activities against P. theae. 16 Major tea leaf volatile constituents, including geraniol, linalool, methyl salicylate, benzyl alcohol, and 2-phenylethanol, were found to exhibit significant antifungal activities toward Colletorichum camelliae Massea. 17 Marine environments, with a wide range of temperature, pressure, salt concentration, and pH, are known to be a rich resource for bioactive natural products.…”

“…To date, there have only been a few reports on active compounds against tea pathogenic fungi. Essential oil-based β-methoxyacrylate derivatives have been synthesized and showed remarkable inhibitory activities against P. theae . Major tea leaf volatile constituents, including geraniol, linalool, methyl salicylate, benzyl alcohol, and 2-phenylethanol, were found to exhibit significant antifungal activities toward Colletorichum camelliae Massea .…”