Design, Synthesis, Acaricidal Activities, and Structure–Activity Relationship Studies of Oxazolines Containing Ether Moieties

• Published in: Journal of agricultural and food chemistry 2022-10, Vol.70 (42), p.13538-13544
• Main Authors: Zhang, Yu, Chen, Yuming, Xun, Xiwei, Chen, Shilin, Liu, Yuxiu, Wang, Qingmin
• Format: Article
• Language: English
• Subjects: Agricultural and Environmental Chemistry
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.2c04628

To develop highly efficient and low cost acaricides, a series of 2,4-diphenyl-1,3-oxazolines containing an ether moiety at the para position of the 4-phenyl group were synthesized from different alcohols and phenols. The bioassay results showed that most of the compounds, especially the short-chain alkyl ethers, exhibited excellent acaricidal activity against both the larvae and the eggs of Tetranychus cinnabarinus. In particular, the n-propyl ether compound Ic possessed much better larvicidal activity (LC50 = 0.0015 mg/L) and ovicidal activity (LC50 = 0.0008 mg/L) than commercial acaricide etoxazole (LC50 = 0.0145 and 0.02 mg/L for larvae and eggs, respectively). In addition, some compounds also exhibited insecticidal activity, especially compound Iw (4-CF3-phenyl ether) showed higher mortality than etoxazole against Mythimna separata, Helicoverpa armigera, and Pyrausta nubilalis. Considering the high acaricidal activity and relatively low cost, Ic was worthy of further study as an acaricide agent. An alternative synthetic route for the large-scale synthesis of Ic was then studied.