Insecticidal effect of new synthesized chalcone derivatives on Caribbean fruit fly, Anastrepha suspensa

Authors: YUCETEPE, SUMEYYA - Marmara University; KAYMAKCIOGLU, BEDIA - Biruni University; Yang, Xiangbing; Tabanca, Nurhayat; TOK, FATIH - Marmara University

Submitted to: Zeitschrift Fur Naturforschung
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 4/18/2024
Publication Date: 5/3/2024
Citation: Yucetepe, S., Kaymakcioglu, B.K., Yang, X., Tabanca, N., Tok, F. 2024. Insecticidal effect of new synthesized chalcone derivatives on Caribbean fruit fly, Anastrepha suspensa. Zeitschrift Fur Naturforschung. https://doi.org/10.1515/znc-2024-0005.
DOI: https://doi.org/10.1515/znc-2024-0005

Interpretive Summary: Chalcones are widely distributed in plants and display a wide range of insecticide activities. Currently, management of tephritid fruit flies, such as Caribbean fruit fly (CFF), in subtropical agriculture are facing concerns like the toxicity of many synthetic insecticides on human health, the environment, and the development of resistance in insect pests. To develop new and biorational biopesticide, scientists from Marmara University (Turkey), Biruni University (Turkey), and the USDA-ARS (Miami, Florida) designed and synthesized fourteen new series of chalcone derivatives (1-14) to evaluate their safety to the environment and their toxicities against female CFFs. Results showed there was only one derivative 2 in 73% mortality at 100 ug/fly after 24 hrs. This study revealed that derivative 2 showed great potential to be further designed and synthesized as novel and environmentally safe insecticide to control Tephritid fruit flies, such as A. suspensa in Subtropical and tropical agriculture in USA.

Technical Abstract: In this study, 14 new series of chalcone derivatives were synthesized from the nucleophilic addition reaction of 4-aminoacetophenone, various isocyanate molecules, and the chemical structures of the synthesized compounds were confirmed using IR, 1H-NMR, 13C-NMR spectroscopy, and elemental analysis. In silico studies were carried out to investigate the toxic risks of synthesized chalcone compounds to humans and the environment. Moreover, the potential of the 14 chalcone derivatives was evaluated using topical bioassays for their insecticidal activities against the adult female Caribbean fruit fly, Anastrepha (A.) suspensa, one of the most economically important tephritid fruit flies in tropical and subtropical regions of North America. According to the in silico study, the synthesized compounds were found to have good bioconcentration factors and IGC50 values, except for derivative 14. Results of the toxicity tests showed that chalcone derivatives are effective against female A. suspensa. Among the synthesized chalcones, derivative 2 exhibited the greatest insecticidal activity, resulting in 73% mortality at 100 µg/fly after 24 hrs, whereas other derivatives showed less than 30% mortality. Our results demonstrate that insecticidal activity may be modulated by the presence of a certain phenyl ring in the structure of derivative 2, and therefore has potential for design of efficient biorational chemicals for tephritid fruit fly management.