The low utilization efficiency of pesticides exerts an adverse impact on the environment and human health. Polymer-related controlled-release nanosized pesticide systems provide a promising and efficient way to overcome the problem. In this work, a biodegradable and light-responsive amphiphilic polymer was synthesized via 1,1,3,3-tetramethylguanidine-promoted polyesterification under mild conditions (low temperature, no vacuum, and no inert gas protection). We used this polymer to fabricate a light-triggered controlled-release nanosized pesticide system. The herbicide, 2,4-dichlorophenoxyacetic acid (2,4-D), was selected as a model drug to show its potential as a controlled-release pesticide system. It was found that the 2,4-D-loaded polymeric nanoparticles were stable without the treatment of UV, while the release rate of 2,4-D from the nanoparticles gradually increased after treatment with UV light. Pot trial showed that the 2,4-D-loaded polymer nanoparticles showed a good herbicidal effect. Finally, toxicity studies suggested that the polymer can reduce toxicity to nontarget organisms.

A synthetic route to prepare a poly(ethylene glycol) with a single cinnamaldehyde acetal unit in the polymer chain, was successfully established using a newly synthesized cinnamaldehyde acetal diethylene glycol (CADEG) as initiator. This HO-PEG(ca)-OH is non-toxic and would be degraded into a cinnamaldehyde and two PEG diols in acid environment. A whole polyethylene glycol based hydrogel was easily fabricated by thiol-ene “click” reaction in alkalescence aqueous solution using acrylate-PEG(ca)-acrylate and 4-arm PEG-SH as raw materials at room temperature. The gel time was dependent on the pH of the solution and its alkalinity can promote gel. The hydrogel can be degradable in acidic conditions and the stronger the acidity, the faster the degradation. This HO-PEG(ca)-OH also can be used in synthesis of cinnamaldehyde containing PEG derivatives, block copolymers or other acid degradable materials.

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Photo and acid dual degradable polymeric nanoparticles.

An o-nitrobenzyl dithiol and a group of diacrylates containing one or two functional groups were designed for facile synthesis of a series of linear photo-labile functional and heterobifunctional poly(β-thioester)s via thiol-ene click polymerization. These o-nitrobenzyl thioether-containing polyesters show excellent photo-degradation properties under UV light. Photoresponsive polymeric nanoparticles from a functional polyester exhibit good weeding performance as a herbicide delivery system. The possible photo-degradation mechanism of the polyesters was studied and proposed. The o-nitrobenzyl dithiol and its corresponding photo-labile polyesters could be used in smart drug or pesticide delivery, photo-labile graft copolymers synthesis, and even photolithography.