Application of TNB in dual photo-controlled release of phenamacril, imidacloprid, and imidacloprid synergist

Qi Yin; Wen Fu; Xinyue Hu; Zhiping Xu; Zhong Li; Xusheng Shao

doi:10.1111/php.13934

Application of TNB in dual photo-controlled release of phenamacril, imidacloprid, and imidacloprid synergist

Photochem Photobiol. 2024 Mar 6. doi: 10.1111/php.13934. Online ahead of print.

Authors

Qi Yin¹, Wen Fu¹, Xinyue Hu¹, Zhiping Xu¹, Zhong Li^{1

2}, Xusheng Shao^{1

2

3

4}

Affiliations

¹ Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai, China.
² State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, China.
³ Shanghai Frontier Science Research Base of Optogenetic Techniques for Cell Metabolism, School of Pharmacy, East China University of Science and Technology, Shanghai, China.
⁴ Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, China.

PMID: 38445797
DOI: 10.1111/php.13934

Abstract

Pesticides can improve crops' yield and quality, but unreasonable applications of pesticides lead to waste of pesticides which are further accumulated in the environment and threaten human health. Developing the release of controlled drugs can improve the utilization rate of pesticides. Among these methods, light-controlled release is a new technology of controlled release, which can realize spatiotemporal delivery of drugs by light. Four compounds, named Imidacloprid-Thioacetal o-nitrobenzyl-Phenamacril (IMI-TNB-PHE), Imidacloprid-Thioacetal o-nitrobenzyl- Imidacloprid (IMI-TNB-IMI), Phenamacril-Thioacetal o-nitrobenzyl-Phenamacril (PHE-TNB-PHE), and Imidacloprid-Thioacetal o-nitrobenzyl-Imidacloprid Synergist (IMI-TNB-IMISYN), were designed and synthesized by connecting thioacetal o-nitrobenzyl (TNB) with pesticides TNB displaying simple and efficient optical properties in this work. Dual photo-controlled release of pesticides including two molecules of IMI or PHE, both IMI and PHE, as well as IMI and IMISYN were, respectively, studied in this paper. Insecticidal/fungicidal activities of the photosensitive pesticides showed 2-4 times increments if they were exposed to light. In addition, a synergistic effect was observed after the light-controlled release of IMI-TNB-IMISYN, which was consistent with the effect of IMISYN. The results demonstrated whether dual photo-controlled release of the same or different pesticide molecules could be achieved with a TNB linker with spatiotemporal precision. We envisioned that TNB will be an innovative photosensitive protective group for light-dependent application of agrochemicals in the future.

Keywords: TNB; dual photo-controlled release; fungicide; insecticide; synergist.

Abstract

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