Synthesis of phthalimide derivatives and their insecticidal activity against caribbean fruit fly, Anastrepha suspensa (Loew)

Authors: TOK, FATIH - Marmara University; Yang, Xiangbing; Tabanca, Nurhayat; KOCYIGIT-KAYMAKCIOGL, BEDIA - Marmara University

Submitted to: Biomolecules EISSN 2218-273X
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 2/2/2023
Publication Date: 2/14/2023
Citation: Tok, F., Yang, X., Tabanca, N., Kocyigit-Kaymakciogl, B. 2023. Synthesis of phthalimide derivatives and their insecticidal activity against caribbean fruit fly, Anastrepha suspensa (Loew). Topic Issue: Frontiers in Chemical Ecology. Biomolecules EISSN 2218-273X. 13(2): 361. https://doi.org/10.3390/biom13020361.
DOI: https://doi.org/10.3390/biom13020361

Interpretive Summary: Tephritid fruit flies are major insect pests that damage fruit crops all over the world. Current pest management relies on bait sprays or bait stations that incorporate insecticides. However, extensive use of conventional insecticides has resulted in the development of pesticide resistance in fruit fly populations and negative impacts to the environment. Therefore, environmentally sound alternatives are urgently needed. In this study, scientists from Marmara University (Turkey) and the USDA-ARS (Miami, FL) designed and synthesized thirteen phthalimide derivatives (4a-4m) and evaluated their safety to the environment, and their toxicities against female Caribbean fruit flies (Anastrepha suspensa) in laboratory bioassays. Results showed that three compounds (4a, 4c, and 4d) exhibited potent insecticidal activity, yet posed low risk to the environment. This study revealed some key structural features of the derivatives that were responsible for toxicity, and identified promising candidates for development of novel environmentally friendly insecticides for use in management programs for pest tephritid fruit flies, such as A. suspensa.

Technical Abstract: In this study, thirteen phthalimide derivatives were designed and synthesized. All synthesized compounds were evaluated to determine their potential for inhibitory activities against females of the Caribbean fruit fly, Anastrepha suspensa (Loew) (Diptera: Tephritidae). These efforts led to the discovery of three compounds 4a, 4c and 4d with potent insecticidal activity (LD50 range from 0.70 to 1.91 ug/fly). Among these compounds, 4a exhibited the highest inhibitory potency with 0.70 ug/fly. In addition, in silico models indicated that compound 4a is less toxic than phthalimide and other precursors. Therefore, our results suggest that 4a has strong potential as a candidate component for developing a novel environmentally friendly insecticide for control of pest fruit flies.