Search Results (12)

In our ongoing work to create potential antifungal agents, we synthesized and tested a group of C1-substituted acylhydrazone β-carboline analogues 9a–o and 10a–o for their effectiveness against Valsa mali, Fusarium solani, Fusarium oxysporum, and Fusarium graminearum. Their compositions were analyzed using different spectral techniques, such as ¹H/¹³C NMR and HRMS, with the structure of 9l being additionally confirmed through X-ray diffraction. The antifungal evaluation showed that, among all the target β-carboline analogues, compounds 9n and 9o exhibited more promising and broad-spectrum antifungal activity than the commercial pesticide hymexazol. Several intriguing findings regarding structure–activity relationships (SARs) were examined. In addition, the cytotoxicity test showed that these acylhydrazone β-carboline analogues with C1 substitutions exhibit a preference for fungi, with minimal harm to healthy cells (LO2). The reported findings provide insights into the development of β-carboline analogues as new potential antifungal agents. Full article

Luobuma (Apocynum venetum and Poacynum hendersonni) is widely cultivated for environmental conservation, medicinal purposes and the textile industry. In 2018, a severe leaf spot disease that attacked the leaves of Luobuma was observed in plants cultivated in Yuzhong County, Gansu Province, China. Symptoms of the disease appeared as white or off-white spots surrounded by brown margins on the leaves of A. venetum. The spots expanded and covered a large area of the leaf, presenting as “cankers” with progression of the disease, leading to leaf death. The initial symptoms of the disease on P. hendersonni were similar to the symptoms of A. venetum, with a larger disease spot than A. venetum, and the spot was black and thicker. The aim of this study was to identify the fungal species and evaluate the effectiveness of fungicides (hymexazol and zhongshengmycin) against the pathogen in vitro. The fungi species that caused the new disease was identified as Alternaria tenuissima based on the morphological characteristics, pathogenicity tests, and phylogenetic analysis of the internal transcribed spacer (ITS) region, glyceraldehyde 3-phosphate dehydrogenase (gpd), translation elongation factor 1-alpha (TEF) and the histone 3 (H3) gene sequences. The findings showed that hymexazol fungicide can be used to control leaf spot disease. This is the first report on Luobuma leaf spot disease caused by A. tenuissima in China. Full article

To explore more efficient and less toxic antibacterial and antifungal pesticides, we utilized 2,6-difluorobenzamide as a starting material and ultimately synthesized 23 novel benzoylurea derivatives containing a pyrimidine moiety. Their structures were characterized and confirmed by ¹H NMR, ¹³C NMR, ¹⁹F NMR, and HRMS. The bioassay results demonstrated that some of the title compounds exhibited moderate to good in vitro antifungal activities against Botrytis cinerea in cucumber, Botrytis cinerea in tobacco, Botrytis cinerea in blueberry, Phomopsis sp., and Rhizoctonia solani. Notably, compounds 4j and 4l displayed EC₅₀ values of 6.72 and 5.21 μg/mL against Rhizoctonia solani, respectively, which were comparable to that of hymexazol (6.11 μg/mL). Meanwhile, at 200 and 100 concentrations, the target compounds 4a–4w exhibited lower in vitro antibacterial activities against Xanthomonas oryzae pv. oryzicola and Xanthomonas citri subsp. citri, respectively, compared to those of thiodiazole copper. Furthermore, the molecular docking simulation demonstrated that compound 4l formed hydrogen bonds with SER-17 and SER-39 of succinate dehydrogenase (SDH), providing a possible explanation for the mechanism of action between the target compounds and SDH. This study represents the first report on the antifungal and antibacterial activities of novel benzoylurea derivatives containing a pyrimidine moiety. Full article

Soybean root rot is an important disease that has affected soybean crops in recent years, but the available control methods still do not provide good protection for soybeans. In this study, three biodegradable mulch films (HML@CMCS, HML@PVA, HML@CMCS/PVA) were prepared from carboxymethyl chitosan (CMCS) and polyvinyl alcohol (PVA), and hymexazol (HML) was loaded on them. The surface and cryofractured surface were compared via micromorphological observations using SEM, AFM, and 3D measurements. Mechanical, water barrier, and optical properties were compared between the different films, and the results showed that the composite film (HML@CMCS/PVA) had better tensile properties, lower water content (35%), and lower water solubility (28%), while water barrier properties were significantly improved. HML@CMCS/PVA also had better light transmission than commercial films (opacity at 600 nm of 1.92). Finally, the composite film was selected to study antifungal properties, soil degradability, and biosafety. The results showed that it exhibited significant inhibitory activity against Fusarium oxysporum and could effectively control soybean root rot, while degradation reached 58% after 7 d of soil burial, and the mortality of earthworms relative to the microplastics produced by the film within 7 d (23.33%) was much lower than that of the commercial film, demonstrating its excellent biosafety. This study provides a new approach for the on-farm management of soybean root rot and the reduction in soil microplastic pollution. Full article

As a famous street tree, camphor (Cinnamomum camphora) is widely planted worldwide. However, in recent years, camphor with root rot was observed in Anhui Province, China. Based on morphological characterization, thirty virulent isolates were identified as Phytopythium species. Phylogenetic analysis of combined ITS, LSU rDNA, β-tubulin, coxI, and coxII sequences assigned the isolates to Phytopythium vexans. Koch’s postulates were fulfilled in the greenhouse, and the pathogenicity of P. vexans was determined by root inoculation tests on 2-year-old camphor seedlings; the symptoms of indoor inoculation were consistent with those in the field. P. vexans can grow at 15–30 °C, with an optimal growth temperature of 25–30 °C. The results of fungicide sensitivity experiments indicated that P. vexans was the most sensitive to metalaxyl hymexazol, which may be a useful idea for the future prevention and control management of P.vexans. This study provided the first step for further research on P. vexans as a pathogen of camphor, and provided a theoretical basis for future control strategies. Full article

Agents with antifungal activity play a vital role as therapeutics in health care, as do fungicides in agriculture. Effectiveness, toxicological profile, and eco-friendliness are among the properties used to select suitable substances. Furthermore, a steady supply of new agents with different modes of action is required to counter the well-known potential of human and phyto-pathogenic fungi to develop resistance against established antifungals. Here, we use an in vitro growth assay to investigate the activity of the calcineurin inhibitor tacrolimus in combination with the commercial fungicides cyproconazole and hymexazol, as well as with two earlier reported novel {2-(3-R-1H-1,2,4-triazol-5-yl)phenyl}amines, against the fungi Aspergillus niger, Colletotrichum higginsianum, Fusarium oxysporum and the oomycete Phytophthora infestans, which are notoriously harmful in agriculture. When tacrolimus was added in a concentration range from 0.25 to 25 mg/L to the tested antifungals (at a fixed concentration of 25 or 50 mg/L), the inhibitory activities were distinctly enhanced. Molecular docking calculations revealed triazole derivative 5, (2-(3-adamantan-1-yl)-1H-1,2,4-triazol-5-yl)-4-chloroaniline), as a potent inhibitor of chitin deacetylases (CDA) of Aspergillus nidulans and A. niger (AnCDA and AngCDA, respectively), which was stronger than the previously reported polyoxorin D, J075-4187, and chitotriose. The results are discussed in the context of potential synergism and molecular mode of action. Full article

Hymexazol (HYM) is an active ingredient commonly used in a wide variety of crops; however, to date, there are no publications on its dissipation and residuality in strawberry fruits and leaves. The objective of the research was to evaluate the dissipation and residuality of hymexazol in strawberry using a modified QuEChERS method with UHPLC-ESI/MS-MS. For this, several validation experiments using the chromatographic method were conducted. The strawberry crop was established in the field, and the content of the HYM was monitored through several applications. The method showed good linearity (correlation coefficients > 0.9995), accuracy (recoveries in 73.7–109.4%), and sensitivity (limits of quantification 0.017 mg kg⁻¹). Despite the two and four drench-treatments of HYM in the strawberry crop, the compound was not detected at levels above the LOD 24 and 48 h after the last treatment. This is due to various plants metabolizing hymexazol to glucose conjugates of its tautomers, i.e., its O-glucoside and N-glucoside, probably with low or null movement to the aerial parts and fruits of the crop. Full article

The use of synthetic fungicide needs to be gradually reduced because of its adverse effect on human health and the environment. An integrated approach combining fungicides with biological control agents (BCAs) can be used to reduce the fungicide doses, thereby minimizing the risks associated with chemical fungicides. In this study, the combined application of a BCA Trichoderma and a fungicide hymexazol was used to manage the cowpea wilt disease caused by Fusarium oxysporum. The Trichoderma SC012 strain, which is resistant to hymexazol, was screened out and identified as T. asperellum. T. asperellum SC012 showed hyperparasitism to F. oxysporum and could penetrate and encircle the hyphae of pathogen on a medium amended or not with hymexazol. When combined with hymexazol, the population density in the rhizosphere soil of cowpea showed no significant difference compared with the treatment Trichoderma used alone. When the concentration of T. asperellum SC012 or hymexazol was halved, their combined application could control cowpea wilt disease more effectively than their individual use. The findings showed that the combination of Trichoderma and hymexazol could reduce the use of chemical fungicide, which is eco-friendly and may be an important part of integrated control of Fusarium wilt in cowpea. Full article

Based on benzoxazole and benzothiazole scaffold as an important pharmacophore, two series of 2-(aryloxymethyl) benzoxazole and benzothiazole derivatives were synthesized and their antifungal effects against eight phytopathogenic fungi were evaluated. Compounds 5a, 5b, 5h, and 5i exhibited significant antifungal activities against most of the pathogens tested. Especially 5a, 5b, 5h, 5i, 5j, and 6h inhibited the growth of F. solani with IC₅₀ of 4.34–17.61 μg/mL, which were stronger than that of the positive control, hymexazol (IC₅₀ of 38.92 μg/mL). 5h was the most potent inhibitor (IC₅₀ of 4.34 μg/mL) against F. Solani, which was about nine times more potent than hymexazol. Most of the test compounds displayed significant antifungal effects against B. cinerea (IC₅₀ of 19.92–77.41 μg/mL), among them, 5a was the best one (IC₅₀ of 19.92 μg/mL). The structure-activity relationships (SARs) were compared and analyzed. The result indicates that the electron-drawing ability and position of the substituents have a significant impact on biological activities. Furthermore, docking studies were carried out on the lipid transfer protein sec14p from S. cerevisiae, and preliminarily verified the antifungal activities. Taken together, these results provide 2-(phenoxymethyl)benzo[d]oxazole as an encouraging framework that could lead to the development of potent novel antifungal agents. Full article

Replanting obstacles of Panax notoginseng caused by complex factors, including pathogens, have received great attention. In this study, essential oils (EOs) from either Alpinia officinarum Hance or Amomum tsao-ko (Zingiberaceae) were found to inhibit the growth of P. notoginseng-associated pathogenic fungi in vitro. Subsequent GC-MS analysis revealed the chemical profiles of two plant derived EOs. Linalool and eucalyptol were found to be abundant in the EOs and tested for their antifungal activities. In addition, the synergistic effects of A. tsao-ko EOs and hymexazol were also examined. These findings suggested that Zingiberaceae EOs might be a good source for developing new green natural pesticides fighting against root-rot of P. notoginseng. Full article

An efficient synthesis of highly functionalized chiral β-amino ester derivatives containing benzothiophene and benzothiazole moieties is developed by a Mannich-type reaction using a cinchona alkaloid-derived thiourea catalyst. The desired products were obtained in good yields and high enantioselectivities (~86% yield, >99% ee) using to the optimized reaction conditions. The synthesized compounds were characterized by ¹H-NMR, ¹³C-NMR, IR, and HREI-MS analyses. The bioassays identified that compound 5dr has excellent antifungal activity, with a 60.53% inhibition rate against F. oxysporum, higher than that of the commercial agricultural fungicide hymexazol, whose inhibition rate was 56.12%. Full article

A series of new sulfone compounds containing 1,3,4-oxadiazole moieties were synthesized. The structures of these compounds were confirmed by spectroscopic data (IR, ¹H- and ¹³C-NMR) and elemental analyses. Antifungal tests indicated that all the title compounds exhibited good antifungal activities against eight kinds of plant pathogenic fungi, and some showed superiority over the commercial fungicide hymexazol. Among them, compounds 5d, 5e, 5f, and 5i showed prominent activity against B. cinerea, with determined EC₅₀ values of 5.21 μg/mL, 8.25 µg/mL, 8.03 µg/mL, and 21.00 µg/mL, respectively. The present work demonstrates that sulfone derivatives such as 5d containing a 1,3,4-oxadiazole moiety can be used as possible lead compounds for the development of potential agrochemicals. Full article