Abstract
In order to discover novel eco-friendly compounds with good activity for aphid control, (E)-β-farnesene (EβF), the main component of the aphid alarm pheromone, was chosen as the lead compound. By introducing a 2-nitroimino-hexahydro-1,3,5-triazine moiety (abbreviated NHT) to replace the unstable conjugated double bond system of EβF, a series of novel EβF analogues containing the NHT moiety were synthesized via the reaction of substituted NHT rings with (E)-1-chloro-3,7-dimethylocta-2,6-diene. All the compounds were characterized by 1H-NMR, 13C-NMR, IR, and high resolution mass spectroscopy (HRMS). The bioassay results showed that all the analogues displayed different repellent and aphicidal activities against green peach aphid (Myzus persicae). Particularly, the analogue 4r exhibited obvious repellent activity (repellent proportion: 78.43%) and similar aphicidal activity against M. persicae (mortality: 82.05%) as the commercial compound pymetrozine (80.07%). A preliminary structure-activity relationship (SAR) study was also performed, which offered valuable clues for the design of further new EβF analogues.
Highlights
As some of the major pests in agriculture, aphids cause considerable damage [1,2] to crop growth, yield and quality by sucking phloem sap [3], secreting honeydew to induce frequently plant sooty moulds [1,2,4] and transmitting plant viruses [5,6,7]
Traditional aphid control methods have largely relied on agrochemicals, which has led to increasing pest resistance and cross resistance
4 were synthesized the nucleophilic substitution reaction between intermediates32 were prepared by Mannich reactions between nitroguanidine, formaldehyde and different commercially and 3a–3t in acetonitrile using K
Summary
As some of the major pests in agriculture, aphids cause considerable damage [1,2] to crop growth, yield and quality by sucking phloem sap [3], secreting honeydew to induce frequently plant sooty moulds [1,2,4] and transmitting plant viruses [5,6,7]. Owing to the variety of species, large population, fast reproduction and high resistance to chemical insecticides, aphid control has become more and more challenging. As the idea of eco-friendly pest control is increasingly recognized worldwide, the strategy for aphid control has changed from traditional “killing” to rational “regulation” [8]. Traditional aphid control methods have largely relied on agrochemicals, which has led to increasing pest resistance and cross resistance. It is important to develop novel aphid control strategies. Using aphid alarm pheromones could be an alternative way to control their population by manipulating aphid behaviors, and is regarded to be conducive to ecological protection [9,10]
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