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ABSTRACT To explore novel structures of strobilurin fungicides, a series of novel strobilurin derivatives featuring a substituted 1,3,4‐oxadiazole in the side chain were synthesized using an intermediate derivatization method and characterized by nuclear magnetic resonance spectroscopy (NMR) and high‐resolution mass spectrometry (HRMS). The reactions involved in the synthesis process include hydrazine hydrolysis, cyclization, nucleophilic substitution reactions. The raw materials required for these reactions are readily available, and the procedures involved in the reaction process are straightforward. The fungicidal activities of the compounds were tested using the inhibition zone method. The inhibition rate of compound 5f on Magnaporthe oryzae was 81.8% at a concentration of 3.125 mg/L, and the EC50 value (0.3045 mg/L) was better than superior to that of kresoxim‐methyl (0.5247 mg/L). [ABSTRACT FROM AUTHOR]

Background: Although cyanobacteria are recognized as renewable sources of biomass for bioactive compounds, they have received little attention as potential biocontrol agents of foliar plant diseases. Purpose : The purpose of this study was to evaluate the fungicidal efficacy of native toxic Iranian cyanobacteria strain Neowestiellopsis persica strain A1387 against Alternaria porri, which causes onion purple blotch disease, in vitro and under greenhouse conditions. Study design: Various concentrations of 1, 5, 10, 15 and 20 mg/ml of cyanobacterial extracellular products of studied cyanobacteria strain were tested for their antifungal activity. Methods: after cultivation cyanobacteria strain, the amount of total cell dry weight, total phenolic compounds and total alkaloid compounds were evaluated. Results: The amount of total biomass, phenolic and Alkaloid compounds was equal to 26.2 ± 0.05 mg/ml, 70.08 ± 0.62 mg/g and 4.24 ± 0.18 mg/g respectively. Identification of compounds using GC-MS showed that Quercetin (28.56147%) and Caffeic acid and Kaempferol (9.275864 and 9.94034%) were the highest and lowest of phenolic compounds respectively, Moreover 1,2-dideuterio-1-deuteriooxy-N-methyl-1-phenylpropan-2-amine; hydrochloride (28.56147%) and Pseudoephedrine (10.67333%) were the highest and lowest of alkaloid compounds. Treatment of infected onion plant with cyanobacterial extract significantly reduced the increase of malondialdehyde and hydrogen peroxide. Also, severity of pathogenicity with Alternaria porri was significantly reduced to 20-50% by applying the 15 and 20 mg/ml of cyanobacteria extract. Conclusion: In conclusion, extracellular metabolites of cyanobacteria extract have potential as effective fungicides to control purple blotch disease of onion.

A guanidine compound was isolated and identified from Buthus martensii Karsch. Based on its characteristic structure, we used it as a lead compound to carry out structural optimization and subsequent fungicidal evaluation. Here 18 guanidine derivatives were designed and synthesized by a facile method, and their structures were characterized by 1H, 13C NMR, and HRMS. Biological assay indicated that most of the title compounds possess potential fungicidal activities against Alternaria altanata, and Penicillium digitatum. Especially, 5a, 5d, and 5i showed inhibition rates (IR) of 41.9, 41.9, and 44.2% respectively against P. digitatum at a concentration of 25 mg/L, whose activities surpassed that of hymexazol. This is the first report on the active derivatives from B. martensii in application of plant protection, providing scientific references for the development and utilization of active ingredients from scorpions. [ABSTRACT FROM AUTHOR]

The commercially available dimethomorph is a mixture of two isomers, among which Z‐ dimethomorph has an excellent control effect against oomycetes, while E‐dimethomorph has less fungicidal activity. Therefore, in this paper, a series of novel benzofuran‐modified cinnamamide derivatives were designed and synthesized by "fixing" the cis‐styrene group in Z‐dimethomorph with benzofuran group. And the modification of the molecular structure of cinnamamide compounds could be beneficial to improve its practical application performance. The synthesized products were evaluated for their antifungal activity against 7 strains of phytopathogenic fungi. It was found that the antifungal spectrum and fungicidal activities of some compounds were improved compared with the commercial fungicides dimethomorph and flumorph. Furthermore, for benzofuran‐modified cinnamamide derivatives, substituted bis‐methoxy in the phenyl ring of cinnamate is crucial to inhibit Phytophthora infestans and Phytophthora dreschsleri. [ABSTRACT FROM AUTHOR]

A total of 38 new benzohydrazide derivatives bearing the 4-aminoquinazoline moiety were designed and synthesized based on the active subunit combination approach and tested in detail for their inhibition activities against eight agricultural phytopathogenic fungi. The bioassay results indicated that many of the synthesized compounds exhibited extraordinary fungicidal activities in vitro against the tested fungi. For example, compounds A5 , A6 , A11 , and A17 had EC 50 (half-maximal effective concentration) values of 0.66, 0.71, 0.40, and 0.42 μg/mL against Colletotrichum gloeosporioides , respectively, comparable to that of boscalid (0.36 μg/mL) and much superior to that of carbendazim (6.96 μg/mL). Of particular importance was that compound A6 with a 3,4-difluorophenyl group was found to possess good broad-spectrum antifungal effects, with EC 50 values ranging from 0.63 to 3.82 μg/mL against the tested eight fungi. In vivo antifungal assays also revealed that compound A6 had good curative and protective efficacies of 72.6% and 78.9% at 200 μg/mL against Rhizoctonia solani -caused rice sheath blight, higher than those of boscalid (70.7 and 65.2%, respectively). Moreover, the mechanism-of-action studies revealed that compound A6 disrupted the cell membrane integrity of R. solani , as proved by relative conductivity measurements, leakage of cellular contents, fluorescence microscopy, and scanning electron microscopy observations. Significantly, this compound also exhibited an effective inhibition of succinate dehydrogenase (SDH) from R. solani (half-maximal inhibitory concentration/IC 50 = 11.02 μM), slightly weaker than that of the SDH inhibitor boscalid (5.17 μM). Further molecular docking analysis revealed that compound A6 could form strong interactions with the key residues of SDH enzyme via hydrogen bond, electrostatic, and π-cation interactions, holding promise for acting as new fungicide leads targeting SDH. Finally, the safety assessments indicated that compound A6 was safe for rice and honeybees.

Investigations into the potential application of nanoparticles acting as nanofungicides in sustainable agriculture are rapidly expanding due to the high antimicrobial properties of these compounds, which do not risk inducing pathogen resistance to fungicides. A detailed understanding of the impact of copper oxide nanoparticles (CuO NPs) on soil-borne phytopathogenic fungi is yet to be obtained. This study aimed to explore the in vitro antifungal activity and control efficacy of CuO NPs applied via irrigation with respect to tobacco black shank (TBS) disease caused by Phytophthoranicotianae. The results revealed that CuO NPs greatly interfered with the reproductive growth process of this fungus, repressing hyphal growth, spore germination and sporangium production. Additionally, morphological damage, intracellular ROS accumulation and increased SOD enzyme activity in hyphae were the antifungicidal mechanisms of these NPs. In pot experiments, treatment with CuO NPs at 100 mg L−1 significantly suppressed TBS development, compared with the effect on control plants, and the control efficacy reached 33.69% without inducing phytotoxicity. Exposure to CuO NPs significantly activated a series of defense enzymes, and resistance genes in tobacco can further explain the mechanisms by which CuO NPs suppressed fungal infection. The Cu content in both the leaves and roots of P. nicotianae-infested plants increased by 50.03 and 27.25%, respectively, after treatment with 100 mg L−1 CuO NPs, compared with that of healthy plants. In particular, a higher Cu content was observed in infected roots than in leaves. Therefore, this study showed the potential of CuO NPs applied as nanofungicides and as nanoinducers of fungus resistance genes for the management of TBS through inhibition of pathogen infection and stimulation of plant defenses.

Bacillus amyloliquefaciens NCPSJ7 showed potential fungicidal activities for the effective control of fungal infection. From the PCR test, the key genes (srfAA, sfp, fenD, bmyB, ituD, and ituC) were detected in B. amyloliquefaciens NCPSJ7. These genes were closely related to the lipopeptides (LPs) synthesis. Next, three LPs families were identified with liquid chromatography–mass spectrometry (LC/MS), including iturin A, fengycin A, and surfactin. After purification with C18, the main active antifungal compound was proven to be C14-iturin A by ESI-HRMS, which has significant activities against fungi. These results proved that C14-iturin A played an important role in inhibiting the growth of fungi for B. amyloliquefaciens NCPSJ7. Furthermore, the isolated LP could inhibit mycelial growth and conidia germination at 30 μg/mL. SEM allowed us to observe that mycelial morphology and conidia germination were also affected. The mycelial ultrastructure TEM observations showed that the external electron-dense outer layer cell wall, which mainly consisted of glycoproteins, was affected. Furthermore, swollen mitochondria, enriched glycogen, and increased vacuoles were also found. LP also affected the intact wall and membranes, leading to their increased permeability, which was proved by propidium iodide (PI) staining and conductivity measurements. Meanwhile, the ergosterol, which has an affinity for iturin A, also increased. These results indicated that LP caused fungal dysfunction and membrane permeability increase, leading to fungal inhibition. Identifying and studying LPs is important in exploring the fungicidal activities of B. amyloliquefaciens, which promotes the use of B. amyloliquefaciens NCPSJ7 as a potential candidate for biocontrol. [ABSTRACT FROM AUTHOR]

Thiasporine A was a natural product containing phenylthiazole ring isolated from the marinederived Actinomycetospora chlora SNC-032 and showed cytotoxicity against the lung cancer cell line H2122. Thiasporine A (4o) and 29 Thiasporine A analogues (3a-3o, 4a-4n) were synthesized using substituted benzonitriles as starting material, among which 24 analogues have not been reported in literature. Their structures were characterized by 1H NMR, 13C NMR and HRMS spectra. The fungicidal activities of Thiasporine A and its analogues were tested. The results indicated that most of Thiasporine A analogues exhibited certain fungicidal activities. Compounds 3e and 3i were found to have the inhibition rates of 84.5% and 84.4% against Rhizoctonia solani at a concentration of 200 μmol/L, with the EC50 values of 17.3 μmol/L and 21.9 μmol/L, respectively. Compounds 4b and 4j displayed the inhibition rate of 100% against Selerotium rolfsii at 200 μmol/L. compound 4b demonstrated an inhibition rate of 83.3% against Phytophthora parasitica at 200 μmol/L, which was better than the commercial thifluzamide. The inhibition rates of compound 3g against five fungi were all higher than 70% at 200 μmol/L. [ABSTRACT FROM AUTHOR]

Bacillus amyloliquefaciens NCPSJ7 showed potential fungicidal activities for the effective control of fungal infection. From the PCR test, the key genes (srfAA, sfp, fenD, bmyB, ituD, and ituC) were detected in B. amyloliquefaciens NCPSJ7. These genes were closely related to the lipopeptides (LPs) synthesis. Next, three LPs families were identified with liquid chromatography–mass spectrometry (LC/MS), including iturin A, fengycin A, and surfactin. After purification with C18, the main active antifungal compound was proven to be C14-iturin A by ESI-HRMS, which has significant activities against fungi. These results proved that C14-iturin A played an important role in inhibiting the growth of fungi for B. amyloliquefaciens NCPSJ7. Furthermore, the isolated LP could inhibit mycelial growth and conidia germination at 30 μg/mL. SEM allowed us to observe that mycelial morphology and conidia germination were also affected. The mycelial ultrastructure TEM observations showed that the external electron-dense outer layer cell wall, which mainly consisted of glycoproteins, was affected. Furthermore, swollen mitochondria, enriched glycogen, and increased vacuoles were also found. LP also affected the intact wall and membranes, leading to their increased permeability, which was proved by propidium iodide (PI) staining and conductivity measurements. Meanwhile, the ergosterol, which has an affinity for iturin A, also increased. These results indicated that LP caused fungal dysfunction and membrane permeability increase, leading to fungal inhibition. Identifying and studying LPs is important in exploring the fungicidal activities of B. amyloliquefaciens, which promotes the use of B. amyloliquefaciens NCPSJ7 as a potential candidate for biocontrol.

• Novel 2-substituted acylaminoethylsulfonamides with the taurine scaffold were synthesized as fungicides against Botrytis cinerea. • Compound V-A-12 showed the best activity in vitro with the EC 50 value of 0.66 mg·L−1. • A 3D-QSAR model was developed to identify some key structural features responsible for the potency. • The effeicacy of sulfonamides was verified in the activity evaluation against procymidone-resistant Botrytis cinerea strains. Botrytis cinerea is an economically important fungal pathogen with a host range of over 200 plant species. Unfortunately, gray mold disease caused by B. cinerea has not been effectively controlled because of its high risk for fungicide resistance development. As a part of our ongoing efforts to develop novel sulfonamides as agricultural fungicides against Botrytis cinerea , we introduced 2-aminoethanesulfonic acid (taurine) substructure, designed and synthesized a series of novel 2-substituted acylaminoethylsulfonamides. The newly synthesized sulfonamides were evaluated in vitro and in vivo for their fungicidal activity against Botrytis cinerea , of which the 2-ethoxyacetylamide derivative (V-A-12 , EC 50 = 0.66 mg·L−1) exhibited the highest potency in vitro and superior fungicidal activity compared with procymidone (EC 50 = 1.06 mg·L−1). In vivo bioassay indicated that compound V-A-12 could be effective for the control of tomato gray mold. Moreover, the structure-activity relationship of these sulfonamides was analyzed by establishing a three-dimensional quantitative structure-activity relationship (3D-QSAR) model, which can provide guidance for the development of sulfonamides as fungicides. Finally, the effeicacy of sulfonamide derivatives was again verified in the activity evaluation against resistant Botrytis cinerea strains. These results further enhance the development value of 2-substituted acylaminoethylsulfonamides to control the tomato gray mold. [ABSTRACT FROM AUTHOR]

A series of new strobilurin derivatives bearing different 1,2,3‐triazole side chains were designed and synthesized. The target compounds were characterized by HRMS, 1H NMR, 13C NMR spectra. Among them, the structure of compound 5q was confirmed by X‐ray single crystal diffraction. All of the target compounds were evaluated in vitro for their fungicidal activity against Gibberella zeae, Phytophythora capsici, Alternaria alternate, Botrytis cinerea and Sclerotonia sclerotiorum at a concentration of 25 mg/L. The bio‐assay results exhibited that some of them showed moderate to good fungicidal activity against Phytophythora capsici and Alternaria alternate. The inhibition rates of compound 5f and 5g were up to 73.6% against Phytophythora capsic, which were significantly higher than 42.5% for Difenoconazole. Preliminary structure‐activity relationships (SAR) were also discussed. A series of new strobilurin derivatives, bearing different 1,2,3‐triazole side chains, were designed and synthesized. All of the target compounds were evaluated in vitro for their fungicidal activity against Gibberella zeae, Phytophythora capsici, Alternaria alternate, Botrytis cinerea and Sclerotonia sclerotiorum at a concentration of 25 mg/L. The bio‐assay results showed that some of the target compounds had moderate to good fungicidal activity against Phytophythora capsici and Alternaria alternate. The inhibition rates of compound 5f and 5g are 73.6%, followed by the inhibition rates of compound 5i, 5k, 5m and 5u are 69.1%, and all of them are against Phytophythora capsic, which are significantly higher than 42.5% for Difenoconazole. Preliminary structure‐activity relationships (SAR) were also discussed. [ABSTRACT FROM AUTHOR]

Softwood bark is an important source for producing chemicals and materials as well as bioenergy. Extraction is regarded as a key technology for obtaining chemicals in general, and valorizing bark as a source of such chemicals in particular. In this paper, properties of 237 compounds identified in various studies dealing with extraction of softwood bark were described. Finally, some challenges and perspectives on the production of chemicals from bark are discussed. [ABSTRACT FROM AUTHOR]

Two novel 1,3,4-thiadiazole compounds, C15H10N4S2 (5a) and C18H19N3S2 (5b) were designed and synthesized by reactions of key intermediate 5-(pyridin-4-yl)-1,3,4-thiadiazole-2-thiol and two substituted benzyl chloride (4-t-Bu and 3-CN). The two 1,3,4-thiadiazole structures were confirmed by 1H-NMR, MS, elemental analyses and X-Ray diffraction. Compound 5a is triclinic with space group P-1 and cell constants: a = 6.1426 (7), b = 8.5323 (14), c = 13.840 (2) Å, a = 90.199 (12), ß = 90.002 (11), γ =106.762 (13)°, Dc = 1.484 g/cm³, Z = 2, V = 694.52 (17) ų, the final R = 0.0400 and wR = 0.111 for 1786 observed reflections with I > 2s(I). Compound 5b is triclinic with space group P2(1)/c and cell constants: a = 10.490 (5), b = 19.818 (10), c = 8.825(5) Å, a = 90, ß = 98.989(10), γ =90°, Dc = 1.252 g/cm³, Z = 4, V = 1812.2(16) Å3, the final R = 0.0630 and wR = 0.192 for 2023 observed reflections with I > 2s(I). Theoretical calculation was carried out by DFT method using 6-31G basis set. The compounds also possessed moderate fungicidal activity. [ABSTRACT FROM AUTHOR]

The novel fungicidal agents, ( E)-5-[1-(2-oxo-1-oxaspiro[4,5]dec/non-3-en-3-yl)ethylidene]-2-aminoimidazolin- 4-one derivatives, were designed and synthesized in moderate to excellent yields in four steps using α-hydroxyketone and diketene as raw materials and characterized by HR-ESI-MS, 1H NMR and X-ray diffraction. The preliminary bioassay showed that some of these compounds, such as 5e, 6a, 6e, and 7 h exhibit 87.8%, 91.3%, 89.9% and 87.8% inhibition rates against Sclerotinia scleotiorum, 3b, 3c, 4c and 7 h exhibit 96.4%, 92.5%, 90.3% and 76.9% inhibition rates against Phytophthora capsici at the concentration of 50 µg/ mL, respectively. These compounds exhibited significant fungicidal activities against S. scleotiorum and P. capsici with EC50 values of 2.56-11.60 µg/ mL, and compounds 6e and 7 h exhibited weak inhibition against the spore germination of S. scleotiorum, while the spore germination of P. capsici was strongly inhibited by compound 7 h solution. Scanning electron microscopy ( SEM) and transmission electron microscopy ( TEM) observation indicated that compound 7 h had a significant impact on the structure and function of the hyphal cell wall of P. capsici mycelium. [ABSTRACT FROM AUTHOR]

Mycotoxins viz., aflatoxins, the secondary fungal metabolites, are hepatotoxic, genotoxic, carcinogenic, and teratogenic. According to several studies, mycotoxins have been linked to financial losses in all phases of food and feed production, including crop and animal production, processing, and distribution due to the reduction in crop yield and animal productivity. Due to their widespread existence, Aflatoxin and Fusarium toxins, such as deoxynivalenol and fumonisins, are of particular interest because they can seriously contaminate feed and food, adversely affect farm animals with acute or chronic mycotoxicosis, and affect humans with nausea, vomiting, abdominal pains, and other symptoms of acute liver injury. Consequently, there is an increased need for a revolutionary method for preventing mycotoxins in food and livestock and the effects of current contamination by mycotoxins. Several physical, chemical, and biological techniques exist for mycotoxin decontamination or detoxification. It is a known fact that biological detoxification is highly effective and offers ecological sustainability, applicability over a wide range of mycotoxins, easiness and cost-effectiveness too. Algae and the compounds produced by algae have multiple properties like anti-fungal, anti-oxidants, antibiofilm and many more which can be exploited for many applications, including the detoxification or degradation of toxic components, including mycotoxins. Such compounds include sulphated polysaccharides, β- d -glucans, polyphenolic compounds, etc. Spirulina platensis is one such algae that has been suggested as a possible aflatoxin detoxicant. The focus of this study is on the numerous algal characteristics, particularly those derived from polysaccharides, and their potential utility in the detoxification of mycotoxins. • Wide applications and cost-effectiveness of algal detoxification of mycotoxins makes it a sustainable process • Aflatoxin and Fusarium toxins are of special interest because of their prevalence across the globe • Polysaccharides, particularly sulphated polysaccharides, and antioxidants are abundant in algae. • Aflatoxin breakdown by laccase and algal chlorophyllin is accomplished by spirulina. [ABSTRACT FROM AUTHOR]

In our previous work, two dopamine derivatives with benzothiazole fragment were isolated and identified from Polyrhachis dives (P. dives). Based on their characteristic structure, we used them as lead compound to carry out structural optimization and subsequent fungicidal evaluation. Here 20 dopamine derivatives with benzothiazole fragment were designed and synthesized by a facile method, and their structures were characterized by 1 H-NMR, 13 CNMR and HMRS. In bioassays, most of the title compounds possess potential fungicidal activities against Altenaia alternala (A. alternala) and Botrytis cinerea (B. cinerea). Especially, (E)-N-(2-(benzo[d]thiazol-6-yl)ethyl)-3-(p-tolyl)acrylamide and (E)-N-(2-(benzo[d]thiazol-6-yl)ethyl)-3-(4-(trifluoromethyl)phenyl)acrylamide displayed 29.3 mg/L and 10.7 mg/L EC 50 value against A. alternala, respectively, which possessed equivalent fungicidal activities level to hymexazol., (© 2023 Wiley-VHCA AG, Zurich, Switzerland.)

A series of novel 1,2,4-triazole thione derivatives containing 1,2,3-triazole and substituted piperazine moieties were synthesized via the Mannich reaction of 1,2,3-triazole-containing 1,2,4-triazole thiol intermediates with various substituted piperazines and formaldehyde in high yields. The structures of 14 title compounds were confirmed by melting points, IR,1H NMR,13C NMR, and elemental analysis. The bioassay results showed that some of the title compounds exhibit significant fungicidal activities against several plant fungi at 50 μg/mL, especially trifluoromethyl-containing triazole thione derivative9gshowed broad activities and could be made further structural optimization for novel fungicides innovation research. [ABSTRACT FROM PUBLISHER]

A series of 16 oxime ether derivatives containing 1-aryl-3-oxypyrazoles were synthesised, and the structure of one of them, (E)-methyl 2-(2-({(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy}methyl)phenyl)-2-(methoxyimino)acetate was determined by X-ray diffraction crystallography. Preliminary bioassays indicated that some of these compounds exhibited very good fungicidal activities against Rhizoctonia solani, especially the ester 2-(2-({(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy}methyl)phenyl)-2-(methoxyimino)acetate, which displayed greater activity than control compound pyraclostrobin at a dosage of 0.1 μg mL-1. The relationship between structure and fungicidal activity was discussed. Density functional theory studies of the 3-methyl heterocyclic ester and the 4-chorophenyl heterocyclic N-methylamide were carried out and the results discussed in terms of the wide difference in fungicidal activity shown by each compound. [ABSTRACT FROM AUTHOR]

Twenty-one novel oxime ether strobilurins containing indole moiety, which employed an indole group to stabilize the E-styryl group in Enoxastrobin, were designed and synthesized. The biological assay indicated that most compounds exhibited potent fungicidal activities. The structure-activity relationship study demonstrated that the synthesized methyl 3-methoxypropenoate oxime ethers 7b-e exhibited remarkably high activities among all the synthesized oxime ether compounds 7. Moreover, the fungicidal activities of methyl α-(methoxyimino)benzeneacetate oxime ethers compounds 7f-i and N-methoxy-carbamic acid methyl esters compounds 7j-m showed significant differences compared to the corresponding products of ammonolysis. [ABSTRACT FROM AUTHOR]

BACKGROUND Strobilurins are one of the most important classes of agricultural fungicides. To discover new strobilurin analogues with broad spectrum and high activity, a series of novel oxime ether strobilurin derivatives containing substituted benzofurans in the side chain were synthesised and bioassayed. RESULTS The synthesised compounds were characterised by 1H NMR, 13C NMR, MS and HRMS. Bioassays demonstrated that most target compounds possessed good or excellent fungicidal activities, especially against Erysiphe graminis and Pyricularia oryzae. Furthermore, methyl 3-methoxypropenoate oxime ethers exhibited remarkably higher activities against E. graminis, Colletotrichum lagenarium and Puccinia sorghi Schw. Notably, ( E, E)-methyl 3-methoxy-2-{2-[({[5-fluoro-1-(benzofuran-2-yl)ethylidene]amino}oxy)methyl]phenyl}propenoate (BSF2) and ( E, E)-methyl 3-methoxy-2-{2-[({[5-chloro-1-(benzofuran-2-yl)ethylidene]amino}oxy)methyl]phenyl}propenoate (BSF3) were identified as the most promising candidates for further study. CONCLUSION The present work demonstrates that oxime ether strobilurin derivatives containing benzofurans can be used as possible lead compounds for developing novel fungicides. © 2014 Society of Chemical Industry [ABSTRACT FROM AUTHOR]

Dimethomorph is a kind of cinnamamide fungicide with high fungicidal activities for oomycete diseases. The commercially available dimethomorph is a mixture of two isomers, in which (Z)-dimethomorph possessing higher activity and (E)-dimethomorph possessing lower activity. Herein, we reported the design, synthesis and fungicidal activities of a series of novel indole-modified cinnamamide derivatives, which used the indole group to 'fix' the cis-styrene group in (Z)-dimethomorph. The modification of the molecular structure of cinnamamide compounds could be beneficial to improve its practical application performance. Tested the fungicidal activities, it was found that compounds 8j, 9a, 9e, 9i and 9j showed excellent in vivo fungicidal activities (80-100 %) against Pseudoperonospora cubensis at a concentration of 100 mg L -1 , while dimethomorph and flumorph were noneffective. Moreover, parts of synthesized indole-modified cinnamamide derivatives 8 (8a, 8c, 8d and 8j) and 9 (9c and 9j) exhibited the same in vivo fungicidal activities against Phytophthora infestans with dimethomorph or flumorph at a concentration of 50 mg L -1 with 100 % inhibition. The biological assay results indicated that indole-modified cinnamamide derivatives have promising applications in the prevention and treatment of Phytophthora infestans., (© 2022 Wiley-VHCA AG, Zurich, Switzerland.)

Abstract: Twenty-one novel benzothiophene-substituted oxime ether strobilurins, which employed a benzothiophene group to stabilise the E-styryl group in Enoxastrobin (an unsaturated oxime strobilurin fungicide developed by Shenyang Research Institute of Chemical Industry, China) were designed and synthesised. The biological assay indicated that most compounds exhibited good or excellent fungicidal activities, especially against Colletotrichum lagenarium and Puccinia sorghi Schw. In addition, methyl 3-methoxypropenoate oxime ethers and N-methoxy-carbamic acid methyl esters exhibited good in vivo fungicidal activities against Erysiphe graminis, Colletotrichum lagenarium and Puccinia sorghi Schw. under the tested concentrations. Notably, (E,E)-methyl 3-methoxy-2-(2-((((6-chloro-1-(1H-benzo[b]thien-2-yl)ethylidene)amino)oxy)methyl)phenyl)propenoate (5E) exhibited more potent in vivo fungicidal activities against nearly all of the tested fungi at a concentration of 0.39mg/L compared to Enoxastrobin. [Copyright &y& Elsevier]

An ultrasound-promoted one-pot Passerini/hydrolysis reaction sequence has been developed for the synthesis of trifluoroatrolactamide derivatives using a diverse range of trifluoroacetophenones and isonitriles in acetic acid. Parallel synthesis in a centrifuge tube using a noncontact ultrasonic cell crusher was used in this study as an efficient method for the rapid generation of combinatorial trifluoroatrolactamide libraries, and subsequent bio-chemical evaluation of the resulting compounds indicated that they possessed excellent broad-spectrum fungicidal activities. N-(4-chlorophenyl)-2-(4-ethylphenyl)-3,3,3-trifluoro-2-hydroxypropa-namide and N-(4-chlorophenyl)-3,3,3-trifluoro-2-hydroxy-2-(4-methoxyphenyl)propanamide, in particular, showed significant fungicidal activities against all of the fungal species tested in the current study. [ABSTRACT FROM AUTHOR]

Abstract: The 1,3-diol moiety is present in a number of natural products and has some biological activity. Four symmetric anti-2,4-bis(X-phenyl)pentane-2,4-diols (a, X= p-F; b, X= p-CF3; c, X= m-OMe; d, X= m-CF3) have been characterized by X-ray diffraction, and the results indicated that the dihedral angles between the every two benzene rings in the systems are 34.38(10)°, 39.46(13)°, 23.42(7)°(A), 30.42(7)°(B) and 44.74(9)°, respectively. All of the structures were stabilized by classical intra- and intermolecular hydrogen bonding and some other weak interactions. It was observed that the hydrogen bonding patterns were formed between each single-molecule in compounds a–d, whereas H-bonding dimers were formed in the crystal lattices of both the anti- and syn-2,4-bisphenylpentane-2,4-diols. The four symmetric diaryl 1,3-diols were evaluated alongside several other 1,3-diols as potential antifungal agents, and their in vitro antifungal activities were measured against several fungal species, including Gibberella zeae, Botrytis cinerea, Alternaria alternata and Sclerotonia sclerotiorum. [Copyright &y& Elsevier]

Abstract: A series of novel fluorine-containing mandelic acid amide compounds were designed and synthesized by a facile method, and their structures were characterized by 1H nuclear magnetic resonance (NMR) and high-resolution mass spectrometry. The preliminary in vivo bioassays indicated that some of the title compounds showed excellent fungicidal activities in vivo against Pseudoperonospora cubensis at the dosage of 25mgL−1, which were comparable with the control (Mandipropamid). [Copyright &y& Elsevier]

Antimicrobial properties of sulfur, nitrogen, and oxygen bonded organoboron (III) complexes with biologically potent ligands viz., 2-hydroxy-N-phenyl benzamide hydrazine carboxamide(HO∩N∩OH), 2-hydroxy-N-phenyl benzamide hydrazine carbothioamide (HO∩N∩SH), and 2-hydroxy-N-phenyl benzamide hydrazine carbodithioic acid (HO∩N∩SH), have been studied. The unimolar and bimolar reactions of triisopropoxy borane with dibasic tridentate ligands resulted in the formation of colored solids, which have been characterized by elemental analysis, molecular weight determinations, and conductance measurements. The UV, IR, and NMR (1H, 13C, and 11B) spectral studies indicate a tetra-coordinated geometry for the resulting complexes. The ligands and their complexes have been screened for their fungicidal and bactericidal activities, and the results indicate that they exhibit significant antimicrobial properties. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. [ABSTRACT FROM AUTHOR]

New optically active 2-thio-4-imidazolinones 3 with a chiral carbon at position-3 were synthesized from isothiocyanates 2, which were obtained from aza-Wittig reactions of vinyliminophosphoranes 1 with CS2, with easily accessible chiral (S)- or (R)-amino acid methyl ester hydrochlorides. 2-Methylthio-4H-imidazolin-4-ones 4 were obtained by the S-alkylation of compounds 3 in the presence of K2CO3 causing partial racemization of the enantiomeric pure products. These compounds were identified by MS, IR, 1H NMR, 13C NMR spectroscopy, and elemental analysis. The structures of enantiomers 3c and 3d were also confirmed by X-ray diffraction analysis. The results of preliminary bioassay indicated that compounds 4 exhibited growth inhibition of barnyard grass and cole root and stalk, and fungicidal activities against Fusarium oxysporium, Rhizoctonia solani, Gibberella zeae, Dothiorella gregaria, and Colletotrichum gossypii. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. [ABSTRACT FROM AUTHOR]

To find a new lead compound with high biological activity, a series of N -substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide were designed using linking active substructures method. The target compounds were synthesized from substituted benzoic acid by four steps and their structures were confirmed by 1 H NMR, IR spectrum and elemental analysis. The in vitro bioassay results indicated that some target compounds exhibited excellent fungicidal activities, and the position of the substituents played an important role in fungicidal activities. Especially, compound 5n , exhibited better fungicidal activities than the commercial fungicide flutolanil against two tested fungi Valsa mali and Sclerotinia sclerotiorum , with EC 50 values of 3.44 and 2.63 mg/L, respectively. And it also displayed good in vivo fungicidal activity against S. sclerotiorum with the EC 50 value of 29.52 mg/L. [ABSTRACT FROM AUTHOR]

Novel 5-(2-chlorophenylmethylidene)-2-thio-4-imidazolinones 3 and 2-Alkythio-5-(2-chlorophenylmethylidene)-4H-imidazolin-4-ones 4 have been synthesized via a tandem aza-Wittig reaction to develop more imidazolinones that may possess biological activities. The target compounds were identified by GC-MS, IR, and 1H NMR spectroscopies, and element analysis, and, in the case of 4k, its structure was established by single crystal X-ray diffraction. They showed not only fungicidal activities against Gibberella zeae, Cercospora beticola, Fusarium oxysporium, Rhizoctonia solani, and Botryosphaeria berengeriana, but also growth inhibition of Barnyard grass and Cole root and stalk. [ABSTRACT FROM AUTHOR]

In order to find high acitivity and low toxicity antitumor drug-lead compounds, 13 novel N1-(2-furanidyl)-N3-(O,O-dialkylphosphonyl aryl (alkyl)methoxy-carbonylmethyl)-5-fluorouracils were synthesized via phase-transferred catalytic reactions of chloroacetyloxyalkyl phosphonates 2 with N1-(2-furanidyl)-5-fluorouracil. The structures of the products were confirmed by 1H NMR, 31P NMR, IR, and MS spectra and elemental analyses. The results of preliminary bioassay showed that the new compounds possess some extent of inhibitory effect against HCT-8 and Bel-7402 cell lines and good fungicidal activities. [ABSTRACT FROM AUTHOR]

In search of better bioactive compounds, a series of novel 2,6-bis[(3-aryl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]pyridines 2 were synthesized in high yields by the cyclization of 3-aryl-4-amino-5-mercapto-1, 2, 4-triazoles 1 with 2,6-pyridine dicarboxylic acid. 2 exhibited good fungicidal activities against Cerospora beticola sacc. [ABSTRACT FROM AUTHOR]

Abstract: A novel hydrocarbonoclastic bacterium was isolated from rice rhizospheric soil using an enrichment culture technique. Detailed taxonomic studies identified the organism, designated strain PUP6, as a member of the genus Pseudomonas. The bacterium grew in minimal medium amended with n-alkane members of hydrocarbons, n-dodecane (C12H26), n-hexadecane (C16H34), n-octadecane (C18H38), n-octacosane (C28H58); and petroleum fractions such as crude oil and lubricating oil when provided as sole carbon and energy source. Degradation of these n-alkane hydrocarbons and oils in minimal salts medium by strain PUP6 was estimated using gas chromatography with a flame ionization detector. In addition to its hydrocarbonoclastic properties, this bacterium exhibits a broad spectrum of fungal antibiosis against various phytopathogenic fungi. An antifungal metabolite produced by strain PUP6 was isolated, characterized and identified as phenazine-1-carboxamide on the basis of nuclear magnetic resonance and mass spectroscopic analyses. Strain PUP6 also produced plant-growth-promoting siderophores, indoleacetic acid (IAA), phosphate solubilizing enzymes, and fungal cell wall degrading enzymes such as protease and chitinase. This study can be considered as the first report on n-alkane hydrocarbon and oil degradation by a rhizosphere soil bacterium that exhibits biofertilizing and biocontrol traits. Due to its innate multiple functional traits beyond its role in degradation of hydrocarbons, strain PUP6 may be used as plant-growth-promoting rhizobacterium and biocontrol agent against phytopathogenic fungi. [Copyright &y& Elsevier]

The isothiocyanates 2, obtained from aza-Wittig reactions of vinyliminophosphoranes 1 with CS 2 , reacted with hydrazine to give 3-amino-2-thioxo-4-imidazolidinones 4. One-pot reactions of 4, aromatic isocyanates, Ph 3 P , C 2 Cl 6 , and Et 3 N generated imidazo[2,1-b]-1,3,4-thiadiazol-5(6 H )-ones 7. Compound 7 exhibited good fungicidal activities, especially against Sclerotinia sclerotiorum de Bary and Botrytis Cinerea Pers. [ABSTRACT FROM AUTHOR]

2-Alkylthio-3-phenylamino-5-arylmethylene-4H-imidazol-4-ones5were synthesized by S-alkylation of 3-phenylamino-2-thioxo-4-imidazolidinones4, which were obtained via cyclization of isothiocyanates2with phenylhydrazine in presence of solid potassium carbonate. Compound5exhibited fungicidal activity. [ABSTRACT FROM AUTHOR]

4H-Imidazol-4-ones4or 4(3H)-quinazolinones8were synthesized by base catalytic reactions of 2-mercaptobenzothiazole with carbodiimides2or6, respectively, which were obtained via aza-Wittig reaction of iminophosphorane1or5with aromatic isocyanates.4and8exhibited fungicidal activity. [ABSTRACT FROM AUTHOR]

A series of new 6-alkylamino-3-alkylthio-1-phenyl-1H-pyrazolo[3,4-d] pyrimidin-4(5H)-one derivatives5and6have been rapidly synthesized by a novel solution-phase regioselective synthetic method. Treatment of pyrazole o-aminoester1with dibromotriphenylphosphorane gave iminophosphorane2, which underwent a aza-Wittig reaction with phenyl ioscyanate to provide the carbodiimide3. The latter intermediate reacted with alkylamines and regioselectively provided the 1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one derivatives5and6, some of which exhibited good fungicidal activity. [ABSTRACT FROM AUTHOR]

Enantiomerically pure (R)- and (S)-1-(1H-1,2,4-triazol-1-yl)-2-(4-fluorophenyl)-3-trimethylsilylpropan-2-ol 1 were prepared via an enantioselective Grignard reaction. The absolute stereochemistry of 1 was determined by X-ray analysis. In a comparison of in vitro antifungal activities of the enantiomers, the (-)-enantiomer with the R-absolute configuration was far more potent than the (+)-enantiomer. [Copyright &y& Elsevier]

2-Alkylthio-5-phenylmethylidene-4H-imidazol-4-ones 4 were synthesized by S-alkylation of 2-thioxo-3-aryl-4-imidazolidinones 3 , which were obtained via cyclization of isothiocyanate 2 with aromatic primary amines. 3 and 4 exhibited good fungicidal activity against Physalospora piricola . [ABSTRACT FROM AUTHOR]

The study on reaction of (1-phenyl-3-methylthio-4-cyanopyrazol-5-yl)iminomethylene ethyl ether with compounds containing amino group was discussed in order to understand its reactivity. Some structures of compounds were verified by x-ray crystallographic study. The results of the bioassay showed that some of these compounds showed good fungicidal activities. [ABSTRACT FROM AUTHOR]

4H-Imidazolin-4-ones 3 and 4 were synthesized respectively by base catalytic reactions of 4-methylthiophenol or phenthiol with carbodiimides 2 , which were obtained via aza-Wittig reaction of iminophosphorane 1 with aromatic isocyanates. 3 and 4 exhibited good fungicidal activity against Pellicularia sasakii. [ABSTRACT FROM AUTHOR]

To explore a novel fungicide effectively against cucumber downy mildew (CDM), a series of new arylpyrazole containing pyrimidine ether derivatives were designed and synthesized by employing the intermediate derivatization method (IDM). The structures of synthesized compounds were identified by 1 H NMR, 13 C NMR, elemental analyses, MS, and X-ray diffraction. Bioassays demonstrated that some of the title compounds exhibited excellent fungicidal activities against CDM. Especially, compound 7 (EC 50 = 1.22 mg/L) displayed significantly higher bioactivity than that of commercial fungicides diflumetorim and flumorph and nearly equal effect to that of cyazofamid. The relationship between the structure and fungicidal activity of the synthesized compounds was discussed as well. The study showed that compound 7 was a promising fungicide candidate for further development.

The pyrimidinamine diflumetorim is an ideal template for the discovery of agrochemical lead compounds due to its unique mode of action, novel chemical structure, and lack of reported resistance. To develop a new pyrimidinamine fungicide effective against cucumber downy mildew (CDM), a series of new pyrimidinamine derivatives containing an aryloxy pyridine moiety were designed and synthesized by employing the recently reported intermediate derivatization method (IDM). The structures of all compounds were identified by 1 H NMR, elemental analyses, HRMS, and X-ray diffraction. Bioassays demonstrated that some of the title compounds exhibited excellent fungicidal activities against CDM. Compound 9 gave the best activity (EC 50 = 0.19 mg/L), which is significantly better than the commercial fungicides diflumetorim, flumorph, and cyazofamid. The relationship between structure and fungicidal activity of the synthesized pyrimidinamines was explored. The study showed that compound 9 is a promising fungicide candidate for further development.

In this study, we demonstrate that equol has fungicidal activities against Candida albicans. The minimum inhibitory and minimum fungicidal concentrations of equol against C. albicans were 516 and 1,032 µM, respectively. Two separate viability assays found that equol changed the integrity of the C. albicans cell membrane, possibly by formation of membrane lesions. Scanning electron microscopy demonstrated ultrastructural changes.