Discovery of 1,2,4-Oxadiazole Derivatives Containing Haloalkyl as Potential Acetylcholine Receptor Nematicides

• Published in: International journal of molecular sciences Vol. 24; no. 6; p. 5773
• Main Authors: Luo, Ling, Ou, Yuqin, Zhang, Qi, Gan, Xiuhai
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 17-03-2023; MDPI
• Subjects: 1,2,4-oxadiazole derivatives; acetylcholinesterase; Agricultural chemicals industry; Animals; Antinematodal Agents - pharmacology; Avermectin; Crops, Agricultural; Enzymatic activity; Enzyme activity; Enzymes; Hydrocarbons; Metabolism; Mortality; Nematicides; nematocidal activity; Nematoda; Nematodes; Ontology; Oxadiazoles; Oxadiazoles - pharmacology; Pesticides; tioxazafen; transcriptome; Transcriptomes; Tylenchida; United States; China; nematocidal activity; acetylcholinesterase; 1,2,4-oxadiazole derivatives; tioxazafen; transcriptome
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms24065773

Plant-parasitic nematodes pose a serious threat to crops and cause substantial financial losses due to control difficulties. Tioxazafen (3-phenyl-5-thiophen-2-yl-1,2,4-oxadiazole) is a novel broad-spectrum nematicide developed by the Monsanto Company, which shows good prevention effects on many kinds of nematodes. To discover compounds with high nematocidal activities, 48 derivatives of 1,2,4-oxadiazole were obtained by introducing haloalkyl at the 5-position of tioxazafen, and their nematocidal activities were systematically evaluated. The bioassays revealed that most of 1,2,4-oxadiazole derivatives showed remarkable nematocidal activities against
,
, and
. Notably, compound
showed excellent nematocidal activity against
with LC
values of 2.4 μg/mL, which was superior to that of avermectin (335.5 μg/mL), tioxazafen (>300 μg/mL), and fosthiazate (436.9 μg/mL). The transcriptome and enzyme activity results indicate that the nematocidal activity of compound A1 was mainly related to the compound which affected the acetylcholine receptor of
.