An Effective and Promising Strategy for Plant Protection: Synthesis of L-Carvone-Based Thiazolinone–Hydrazone/Nanochitosan Complexes with Antifungal Activity and Sustained Releasing Performance

Li, Baoyu; Duan, Wengui; Lin, Guishan; Ma, Xianli; Wen, Rongzhu; Zhang, Zhaolei

doi:10.3390/ijms25094595

Open AccessArticle

An Effective and Promising Strategy for Plant Protection: Synthesis of L-Carvone-Based Thiazolinone–Hydrazone/Nanochitosan Complexes with Antifungal Activity and Sustained Releasing Performance

by

Baoyu Li

^1,2,

Wengui Duan

^1,2,*,

Guishan Lin

^1,2,*,

Xianli Ma

^1,2,

Rongzhu Wen

^1,2 and

Zhaolei Zhang

^1,2

¹

School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China

²

Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Nanning 530004, China

^*

Authors to whom correspondence should be addressed.

Int. J. Mol. Sci. 2024, 25(9), 4595; https://doi.org/10.3390/ijms25094595

Submission received: 24 March 2024 / Revised: 17 April 2024 / Accepted: 21 April 2024 / Published: 23 April 2024

(This article belongs to the Section Molecular Plant Sciences)

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Abstract

The development of novel natural product-derived nano-pesticide systems with loading capacity and sustained releasing performance of bioactive compounds is considered an effective and promising plant protection strategy. In this work, 25 L-carvone-based thiazolinone–hydrazone compounds 4a~4y were synthesized by the multi-step modification of L-carvone and structurally confirmed. Compound 4h was found to show favorable and broad-spectrum antifungal activity through the in vitro antifungal activity evaluation of compounds 4a~4y against eight phytopathogenic fungi. Thus, it could serve as a leading compound for new antifungal agents in agriculture. Moreover, the L-carvone-based nanochitosan carrier 7 bearing the 1,3,4-thiadiazole-amide group was rationally designed for the loading and sustained releasing applications of compound 4h, synthesized, and characterized. It was proven that carrier 7 had good thermal stability below 200 °C, dispersed well in the aqueous phase to form numerous nanoparticles with a size of~20 nm, and exhibited an unconsolidated and multi-aperture micro-structure. Finally, L-carvone-based thiazolinone–hydrazone/nanochitosan complexes were fabricated and investigated for their sustained releasing behaviors. Among them, complex 7/4h-2 with a well-distributed, compact, and columnar micro-structure displayed the highest encapsulation efficiency and desirable sustained releasing property for compound 4h and thus showed great potential as an antifungal nano-pesticide for further studies.

Keywords: L-carvone; nanochitosan; thiazolinone–hydrazone; antifungal activity; sustained release

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MDPI and ACS Style

Li, B.; Duan, W.; Lin, G.; Ma, X.; Wen, R.; Zhang, Z. An Effective and Promising Strategy for Plant Protection: Synthesis of L-Carvone-Based Thiazolinone–Hydrazone/Nanochitosan Complexes with Antifungal Activity and Sustained Releasing Performance. Int. J. Mol. Sci. 2024, 25, 4595. https://doi.org/10.3390/ijms25094595

AMA Style

Li B, Duan W, Lin G, Ma X, Wen R, Zhang Z. An Effective and Promising Strategy for Plant Protection: Synthesis of L-Carvone-Based Thiazolinone–Hydrazone/Nanochitosan Complexes with Antifungal Activity and Sustained Releasing Performance. International Journal of Molecular Sciences. 2024; 25(9):4595. https://doi.org/10.3390/ijms25094595

Chicago/Turabian Style

Li, Baoyu, Wengui Duan, Guishan Lin, Xianli Ma, Rongzhu Wen, and Zhaolei Zhang. 2024. "An Effective and Promising Strategy for Plant Protection: Synthesis of L-Carvone-Based Thiazolinone–Hydrazone/Nanochitosan Complexes with Antifungal Activity and Sustained Releasing Performance" International Journal of Molecular Sciences 25, no. 9: 4595. https://doi.org/10.3390/ijms25094595

APA Style

Li, B., Duan, W., Lin, G., Ma, X., Wen, R., & Zhang, Z. (2024). An Effective and Promising Strategy for Plant Protection: Synthesis of L-Carvone-Based Thiazolinone–Hydrazone/Nanochitosan Complexes with Antifungal Activity and Sustained Releasing Performance. International Journal of Molecular Sciences, 25(9), 4595. https://doi.org/10.3390/ijms25094595

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An Effective and Promising Strategy for Plant Protection: Synthesis of L-Carvone-Based Thiazolinone–Hydrazone/Nanochitosan Complexes with Antifungal Activity and Sustained Releasing Performance

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