Structure−Activity Relationship Development of Dihaloaryl Triazole Compounds as Insecticides and Acaricides. 1. Phenyl Thiophen-2-yl Triazoles

Cudworth, Denise P.; Hegde, Vidyadhar; Yap, Maurice C. H.; Guenthenspberger, Katherine A.; Hamilton, Christopher T.; Pechacek, James T.; Johnson, Peter L.; Bis, S. J.; Tisdell, F. E.; Dripps, James E.; Bruce, Timothy J.; Dintenfass, Leonard P.; Gifford, James; Karr, Laura L.; Kempe, Margaret K.; Mccormick, Dlee C.; Schoonover, Joseph R.

doi:10.1021/jf071498s

Cited by 16 publications

(9 citation statements)

References 1 publication

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“…1,2,4-Triazole, an important class of heterocyclic rings, has attracted increasing attention due to their broad activities, such as fungicidal [1,2], insecticidal [3,4], herbicidal [5,6], and bactericidal [7,8]. It may also serve as a plant growth regulatory agent [9] and has excellent potential in the pesticide field.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antifungal and antibacterial activity for novel amide derivatives containing a triazole moiety

Tang

Jin

Mou

et al. 2013

Chemistry Central Journal

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BackgroundPlant fungi (e.g., Pellicularia sasakii, Gibberella zeae, Fusarium oxysporum, and Cytospora mandshurica and Phytophthora infestans) and bacteria (e.g., Ralstonia solanacearum) are extremely difficult to manage in agricultural production. The high incidence of plant mortality and the lack of effective control methods make P. sasakii and R. solanacearum two of the world’s most destructive plant pathogens. Pathogenic fungi and bacteria are responsible for billions of dollars in economic losses worldwide each year. Thus, we designed an active amide structure and synthesized a series of novel amide derivatives containing a triazole moiety to discover new bioactive molecules and pesticides that can act against fungi and bacteria.ResultsA series of amide derivatives containing a triazole moiety were synthesized. All the obtained compounds were characterized through proton and carbon nuclear magnetic resonance spectroscopy, infrared spectroscopy, and elemental analysis. Preliminary antifungal activity test showed that some of the synthesized compounds exhibited moderate antifungal activity against P. sasakii, G. azeae, F. oxysporum, C. mandshurica, and P. infestans at 50 mg/L. Compound 4u displayed more potent antifungal activity against P. sasakii and G. azeae than hymexazol. Preliminary antibacterial activity results showed that some of the synthesized compounds exhibited high anti-bacterial activity against R. solanacearum at 200 mg/L. Compounds 4m and 4q displayed high antibacterial activity against R. solanacearum, with 71% and 65% inhibitory rates, respectively.ConclusionsA series of novel amide derivatives containing 1,2,4-triazole moiety were synthesized through the reaction of intermediate 3 with different acyl chlorides and anhydrous potassium carbonates in anhydrous tetrahydrofuran at 50°C, using 2,4-dichloroacetophenoneas as a starting material. The title compounds exhibited high inhibitory effects against P. sasakii, R. solanacearum, and G. azeae.

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Section: Introductionmentioning

confidence: 99%

Synthesis, antifungal and antibacterial activity for novel amide derivatives containing a triazole moiety

Tang

Jin

Mou

et al. 2013

Chemistry Central Journal

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“…Exhibiting antioxidant , antibacterial , antifungal , antiviral , anesthetic , anti‐inflammatory , insecticidal , and anticancer activities, thiophene derivatives play an important role in searching for novel lead molecules of agrichemicals and pharmaceuticals. In the last decade, some thiophene derivatives, such as thicyofen, ethaboxam, silthiopham, and penthiopyrad, were developed as agrochemicals that effectively control agricultural diseases caused by various plant fungi.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Antifungal Activity of 3‐(Thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one Derivatives Bearing a Carbonic Ester Group

Wang

Ren

Mei

et al. 2018

Journal of Heterocyclic Chem

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A series of 3‐(thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one derivatives bearing a carbonic ester group were designed and synthesized by integrating a thiophene nucleus and a pyrroline‐2‐one scaffold in a single molecular architecture. Their structures were confirmed by IR, 1H‐NMR, EI‐MS, and elemental analyses, and their antifungal activities against Fusarium graminearum (Fg), Rhizoctorzia solani (Rs), and Botrytis cinerea (Bc) were evaluated. The antifungal bioassays indicated that some title compounds exhibited desirable antifungal effects against the tested fungi. Strikingly, the title compounds 4i, 4k, 4n, and 4o showed obvious antifungal activities against Rs, with corresponding EC50 values of 35.26, 33.56, 23.90, and 30.48 μg/mL, respectively, which are better than that of hymexazol (37.86 μg/mL). These results indicated that 3‐(thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one derivatives bearing a carbonic ester group can serve as potential structural templates in the search for novel high‐efficient fungicides.

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“…1,2,4-Triazoles and their condensed derivatives have been investigated due to their wide range of bioactivities, including antimicrobial [5][6][7][8] , analgesic-anti-inflammatory [9] , antifungal [10] , herbicidal [11] , insecticidal activity [12] , anticancer [13,14] , and antigenotoxic activity [15] . It is known that the incorporation of a ferrocene fragment into a molecule of an organic compound often produces unexpected biological activity, likely due to different membrane permeation properties and anomalous metabolism.…”

Section: Introductionmentioning

confidence: 99%

Novel ferrocenyl derivatives exert anti-cancer effect in human lung cancer cells in vitro via inducing G1-phase arrest and senescence

Han

et al. 2013

Acta Pharmacol Sin

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Aim: To investigate the effects of 7 novel 1-ferrocenyl-2-(5-phenyl-1H-1,2,4-triazol-3-ylthio) ethanone derivatives on human lung cancer cells in vitro and to determine the mechanisms of action. Methods: A549 human lung cancer cells were examined. Cell viability was analyzed with MTT assay. Cell apoptosis and senescence were examined using Hoechst 33258 and senescence-associated-β-galactosidase (SA-β-gal) staining, respectively. LDH release was measured using a detection kit. Cell cycle was analyzed using a flow cytometer. Intracellular ROS level was measured with the 2′,7′-dichlorodihydrofluorescein probe. Phosphorylation of p38 was determined using Western blot. Results: Compounds 5b, 5d, and 5e (40 and 80 µmol/L) caused significant decrease of A549 cell viability, while other 4 compounds had no effect on the cells. Compounds 5b, 5d, and 5e (80 µmol/L) induced G 1 -phase arrest (increased the G 1 population by 22.6%, 24.23%, and 26.53%, respectively), and markedly increased SA-β-gal-positive cells. However, the compounds did not cause nuclear DNA frag mentation and chromatin condensation in A549 cells. Nor did they affect the release of LDH from the cells. The compounds significantly elevated the intracellular ROS level, decreased the mitochondrial membrane potential, and increased p38 phosphorylation in the cells. In the presence of the antioxidant and free radical scavenger N-acetyl-L-cysteine (10 mmol/L), above effects of compounds 5b, 5d, and 5e were abolished. Conclusion: The compounds 5b, 5d, and 5e cause neither apoptosis nor necrosis of A549 cells, but exert anti-cancer effect via inducing G 1 -phase arrest and senescence through ROS/p38 MAP-kinase pathway.

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Structure−Activity Relationship Development of Dihaloaryl Triazole Compounds as Insecticides and Acaricides. 1. Phenyl Thiophen-2-yl Triazoles

Cited by 16 publications

References 1 publication

Synthesis, antifungal and antibacterial activity for novel amide derivatives containing a triazole moiety

Synthesis, antifungal and antibacterial activity for novel amide derivatives containing a triazole moiety

Design, Synthesis, and Antifungal Activity of 3‐(Thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one Derivatives Bearing a Carbonic Ester Group

Novel ferrocenyl derivatives exert anti-cancer effect in human lung cancer cells in vitro via inducing G1-phase arrest and senescence

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