Diversity oriented synthesis and SAR studies of new quinazolinones and related compounds as insecticidal agents against Culex pipiens L. Larvae and associated predator

• Published in: Bioorganic chemistry 2023-04, Vol.133, p.106436-106436, Article 106436
• Main Authors: Hekal, Mohamed H., Ali, Yasmeen M., Abdel- Haleem, Doaa R., Abu El-Azm, Fatma S.M.
• Format: Article
• Language: English
• Subjects: Animals; Benzoxazinone; Culex - metabolism; Culex pipiens; Cybister tripunctatus; Insecticidal activity; Insecticides - chemistry; Insecticides - pharmacology; Larva; Quinazolinones; Quinazolinones - chemistry; Quinazolinones - pharmacology; SAR study; Structure-Activity Relationship; Temefos - pharmacology
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2023.106436

[Display omitted] •Novel series of quinazolinone derivatives and related compounds were prepared.•The tested quinazolinone derivatives and related compounds showed high larvicidal efficiency.•Most of tested compounds were safer than temephos when exposed against field strain of non-target C. tripunctatus.•Structure–activity relationship (SAR) was discussed the effect of substituents insertion on the derivatives activities. The ongoing study reports the synthesis, spectroscopic analyses and larvicidal efficacy of novel series of quinazolinone derivatives and related compounds. The structures of the products were confirmed relied on their analytical and spectral data (IR, 1H NMR, and 13C NMR). The spectral documentation promoted the successful isolation of the desirable compounds. The insecticidal activities of the synthesized compounds were assessed against laboratory and field strains of Culex pipiens larvae and a predator from the same ecological niche, Cybister tripunctatus. The results revealed that most of the tested compounds showed high potencies against lab strain of C. pipiens larvae with low resistance ratios in filed strain. In particular, compounds 15, 6 and 16 showed low LC50 values, 0.094, 0.106, 0.129 (µg/mL), respectively against lab strain of C. pipiens larvae. The present study also explored the toxicity of tested compounds against field strain of non-target C. tripunctatus. Most of tested compounds were safer than temephos, especially 15 and 6 with SI/PSF values 96.746 and 83.167, respectively. Structure–activity relationship (SAR) was discussed the effect of substituents insertion on the derivatives activities. Quinazolinone derivatives and related compounds are promising compounds in the mosquito control programs and further studies are recommended to develop more effective derivatives and reveal their mode of action.