Discovery of Pyrido[1,2-a]pyrimidine Mesoionic Compounds Containing Benzo[b]thiophene Moiety as Potential Pesticide Candidates

Abstract

The increasing evolution of insect resistance has made it challenging for traditional insecticides to control the bean aphid (Aphis craccivora Koch). To address this pending issue, a range of pyrido[1,2-a]pyrimidine mesoionic compounds containing benzo[b]thiophene were designed and synthesized. The biological activity test results of the target compounds indicated that they had moderate to outstanding insecticidal activity against the bean aphid (Aphis craccivora) and moderate insecticidal activity against the white-backed planthopper (Sogatella f urcifera). Compound L14 exhibited significant insecticidal activity against A. craccivora, with an LC 50 value of 1.82 μg/mL, which was superior to triflumezopyrim (LC 50 = 4.76 μg/mL). The results of enzyme activity assay showed that compound L14 had a definite inhibitory effect on ATPase. Moreover, the proteomics and docking findings of compound L14 suggested that it may act on the central nervous system of aphids and interact with nicotinic acetylcholine receptors. Therefore, compound L14 is a potentially novel insecticide candidate for further utilization.

A novel push-pull strategy-based aphid control agent: repellency on Myzus persicae and attraction towards Eupeodes corollae from laboratory to field

“…Aphids are one of the most serious agricultural and horticultural pests worldwide (Wang et al 2022;Jiang et al 2023;Gong et al 2023). They are phloem-feeding and cause extensive damage to the yield and quality of crops owing to their sap-sucking behavior and e cient transmission of numerous devastating viruses (Fereres and Moreno 2009;Zhang et al 2022). However, the long-term and excessive use of traditional insecticides has led to the development of pest resistance (Tewary et al 2006a; Bass et al 2014).…”

Design, Synthesis, and Insecticidal Activity of Pyridino[1,2-a]pyrimidines Containing Indole Moeites at the 1-Position

“…Since DuPont officially announced two new insecticides, triflumezopyrim (TFM) and dicloromezotiaz, the mesoionic pyridino­[1,2- a ]­pyrimidine has emerged as a hot structure in the area of insecticide design, with a large number of derivatives based on this structure being continuously reported. − Previous derivatizations performed on this structure mostly occurred at the 3-position of pyridino­[1,2- a ]­pyrimidine, − while the substitution options for the 1-position are limited to common pharmacophores such as 2-chlorothiazole, 2-chloropyridine, and cyano in neonicotinoid insecticides. This is undesirable because the diversity of derivatives is restricted, and these pharmacophores may be responsible for the potential toxicity of mesoionic pesticides to nontarget organisms .…”

Optimization of Osthole in the Lactone Ring as an Agrochemical Candidate: Synthesis, Characterization, and Pesticidal Activities of Osthole Amide/Ester Derivatives and Their Effects on Morphological Changes of Mite Epidermis

“…1−4 Tetranychus cinnabarinus Boisduval (Acari: Tetranychidae) is one of the most harmful mites in the world of agriculture and forest production, with a short life history, high reproductive capacity, and high resistance to many chemical active ingredients. 5−8 Blind pesticide abuse frequently occurs in an effort to increase crop yields, and manage pests and illnesses, which results in the emergence of pest resistance 9,10 and major environmental pollution issues. 11−14 Obviously, the development of new pesticides is still on the way.…”

“…Mythimna separata Walker (Lepidoptera: Noctuidae) is a typical long-distance migratory pest that poses a serious threat to the safe production of maize, wheat, and rice. It has a wide range of occurrences and many generations of damage, leading to crop yield reduction and failure in severe cases. − Tetranychus cinnabarinus Boisduval (Acari: Tetranychidae) is one of the most harmful mites in the world of agriculture and forest production, with a short life history, high reproductive capacity, and high resistance to many chemical active ingredients. − Blind pesticide abuse frequently occurs in an effort to increase crop yields, and manage pests and illnesses, which results in the emergence of pest resistance , and major environmental pollution issues. − Obviously, the development of new pesticides is still on the way. Botanical pesticides can control or obstruct pest development, reproduction, and behavior by nontoxic processes, thereby lowering the use of chemical pesticides, assuring the quality and safety of agricultural goods, and preserving ecological security. − Recently, the discovery of novel pesticides from natural products has received much attention. − …”