Molecules

Research

Jump to: Review

13 pages, 1331 KiB

Open AccessArticle

Synthesis, Antioxidant, and Antifungal Activities of β-Ionone Thiazolylhydrazone Derivatives and Their Application in Anti-Browning of Freshly Cut Potato

by Cong Huang, Yuan Zhong, Rong Zeng, Jie Wang, Qingwen Fang, Shuzhen Xiao, Ji Zhang, Zongde Wang, Shangxing Chen and Dayong Peng

Molecules 2023, 28(18), 6713; https://doi.org/10.3390/molecules28186713 - 20 Sep 2023

Viewed by 770

Abstract

In order to develop a new type of antioxidants with high efficiency, a series of β-ionone thiazolylhydrazone derivatives were designed and synthesized from β-ionone, and their structures were characterized by ¹H-NMR, ¹³C-NMR, FT-IR, and HR-MS. The antioxidant test in vitro indicated [...] Read more.

In order to develop a new type of antioxidants with high efficiency, a series of β-ionone thiazolylhydrazone derivatives were designed and synthesized from β-ionone, and their structures were characterized by ¹H-NMR, ¹³C-NMR, FT-IR, and HR-MS. The antioxidant test in vitro indicated that most of the target compounds had high biological activity. Among them, compound 1k exhibited very strong DPPH (1,1-diphenyl-2-picrylhydrazyl radical)-scavenging activity with a half-maximal effective concentration (IC₅₀) of 86.525 μM. Furthermore, in the ABTS (2,2-azinobis (3-ethylbenzothiazoline-6-sulfonate) diammonium salt)-scavenging experiment, compound 1m exhibited excellent activity with an IC₅₀ of 65.408 μM. Their biological activities were significantly better than those of the positive control Trolox. These two compounds, which have good free-radical-scavenging activity in vitro, were used as representative compounds in the anti-browning experiment of fresh-cut potatoes. The results showed that 1k and 1m had the same anti-browning ability as kojic acid, and they were effective browning inhibitors. In addition, it is well known that microbial infection is one of the reasons for food oxidation. Therefore, we investigated the antifungal activity of 25 target compounds against eight plant fungi at a concentration of 125 mg/L. The results indicated that these compounds all have some antifungal activity and may become new potential fungicides. Notably, compound 1u showed the best inhibitory effect against Poria vaporaria, with an inhibition rate as high as 77.71%; it is expected to become the dominant structure for the development of new antifungal agents. Full article

(This article belongs to the Special Issue Recent Advances in the Synthesis and Biological Studies of Chemical Pesticides)

► Show Figures

Graphical abstract

12 pages, 1295 KiB

Open AccessArticle

Structure-Based Bioisosterism Design, Synthesis, Biological Activity and Toxicity of 1,2,4-Oxadiazole Substituted Benzamides Analogues Containing Pyrazole Rings

by Min-Ting Tu, Ying-Ying Shao, Sen Yang, Bin-Long Sun, Ying-Ying Wang, Cheng-Xia Tan and Xue-Dong Wang

Molecules 2022, 27(15), 4692; https://doi.org/10.3390/molecules27154692 - 22 Jul 2022

Cited by 4 | Viewed by 1420

Abstract

In order to discover pesticidal lead compounds with high activity and low toxicity, a series of novel benzamides substituted with pyrazole-linked 1,2,4-oxadiazole were designed via bioisosterism. The chemical structures of the target compounds were confirmed via ¹H NMR, ¹³C NMR and [...] Read more.

In order to discover pesticidal lead compounds with high activity and low toxicity, a series of novel benzamides substituted with pyrazole-linked 1,2,4-oxadiazole were designed via bioisosterism. The chemical structures of the target compounds were confirmed via ¹H NMR, ¹³C NMR and HRMS analysis. The preliminary bioassay showed that most compounds exhibited good lethal activities against Mythimna separate, Helicoverpa armigera, Ostrinia nubilalis and Spodoptera frugiperda at 500 mg/L. Particularly in the case of Mythimna separate, compound 14q (70%) exhibited obvious insecticidal activity. In addition, compound 14h demonstrated good fungicidal activity against Pyricularia oryae with an inhibition rate of 77.8%, and compounds 14e, 14k, 14n and 14r also showed certain antifungal activities (55.6–66.7%). The zebrafish toxicity test showed that the LC₅₀ of compound 14h was 14.01 mg/L, which indicated that it may be used as a potential leading compound for further structural optimization. Full article

(This article belongs to the Special Issue Recent Advances in the Synthesis and Biological Studies of Chemical Pesticides)

► Show Figures

Figure 1

Review

Jump to: Research

19 pages, 6366 KiB

Open AccessReview

Advancement of Phenoxypyridine as an Active Scaffold for Pesticides

by Yanfei Liu, Bin Fu, Yanjun Xu, Bo Ren and Zhaohai Qin

Molecules 2022, 27(20), 6803; https://doi.org/10.3390/molecules27206803 - 11 Oct 2022

Cited by 4 | Viewed by 1549

Abstract

Phenoxypyridine, the bioisostere of diaryl ethers, has been widely introduced into bioactive molecules as an active scaffold, which has different properties from diaryl ethers. In this paper, the bioactivities, structure-activity relationships, and mechanism of compounds containing phenoxypyridine were summarized, which may help to [...] Read more.

Phenoxypyridine, the bioisostere of diaryl ethers, has been widely introduced into bioactive molecules as an active scaffold, which has different properties from diaryl ethers. In this paper, the bioactivities, structure-activity relationships, and mechanism of compounds containing phenoxypyridine were summarized, which may help to explore the lead compounds and discover novel pesticides with potential bioactivities. Full article

(This article belongs to the Special Issue Recent Advances in the Synthesis and Biological Studies of Chemical Pesticides)

► Show Figures