Novel phthalimide derivatives and their toxicities against caribbean fruit fly, anastrepha suspensa (Loew)

Authors: Tabanca, Nurhayat; TOK, FATIH - Marmara University; KOCYIGIT-, KAYMAKCIOGLU B. - Marmara University; Yang, Xiangbing

Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: 5/17/2023
Publication Date: 8/15/2023
Citation: Tabanca, N., Tok, F., Kocyigit-, K., Yang, X. 2023. Novel phthalimide derivatives and their toxicities against caribbean fruit fly, anastrepha suspensa (Loew). National Meeting & Exposition of the American Chemical Society (Hybrid).

Interpretive Summary: Abstract only.

Technical Abstract: Fruit flies (Diptera: Tephritidae) are serious pests of numerous fruit crops throughout the world. Current management typically relies on bait sprays or bait stations that incorporate insecticides, but there are public concerns regarding their adverse effects on the environment and non-target organisms, as well as an increase in resistance to conventional insecticides. Therefore, the need to explore novel, environmentally-friendly and cost-effective alternatives is urgently needed. The isoindoline-1,3-diones, commonly known as phthalimides, are a class of compounds with widespread biological uses, including human medicinal applications. In this study, we designed and synthesized 13 new phthalimides (4a to 4m) with 75-85% yield and characterized these compounds by IR, 1H-NMR, and 13C-NMR spectroscopy. The infrared spectra (IR) of the new phthalimides were detected in N-H stretching vibrations at 3242-3389 cm-1, and carbonyl (C=O) bands of the phthalimide and amide structures were found at 1720-1797 cm-1and 1643-1697 cm-1, respectively. The proton nuclear magnetic resonance spectra (1H-NMR) of 4 (a–m) showed that NH peaks of amide and hydrazide structures resonated as singlets within the range of 11.20-11.40 ppm and 10.37-10.81 ppm, respectively. The carbon-13 nuclear magnetic resonance spectra (13C-NMR) of 4 (a–m) showed that the carbonyl (C=O) carbons of amide and phthalimide structures were in the range of 165.01-169.32 ppm. All molecules were evaluated for their insecticidal activity against female Caribbean fruit fly, Anastrepha suspensa (Loew). High topical toxicities were observed with three phthalimide derivatives (4a, 4c, and 4d) with LD50 values ranging from 0.70 to 1.91 ug/fly within 24 h. This is likely due to the faster permeation of these derivatives through the insect cuticle. Results indicated that lipophilic compounds, which can penetrate the cuticle and pass through cell membranes (lipid bilayers), displayed the greatest level of toxicity against adult A. suspensa. Additional studies are needed to determine potential synergistic effects of two or more phthalimide compounds, and to develop protocols to implement these agents in integrated pest management (IPM) programs for control of tephritid pests.