Synthesis, Insecticidal Activity, and QSAR of Novel Nitromethylene Neonicotinoids with Tetrahydropyridine Fixed cis Configuration and Exo-Ring Ether Modification

Abstract

To keep the nitro group in the cis position, a series of nitromethylene neonicotinoids containing a tetrahydropyridine ring with exo-ring ether modifications were designed and synthesized. All of the compounds were characterized and confirmed by 1H NMR, high-resolution mass spectroscopy, elemental analysis, and IR. The bioassay tests showed that some of them exhibited good insecticidal activities against pea aphids. On the basis of 10 nitromethylene derivatives, the quantitative structure-bioactivity relationship (QSAR) was analyzed and established. The results suggested that AlogP98 and Dipole_Mopac might be the important parameters related with biological activities.

Overall status of neonicotinoid insecticides in China: Production, application and innovation

“…Recently, some potential neonicotinoids with cis-configuration have been synthesized and shown insecticidal activity in a wide range of insects, including N. lugens. [30][31][32] An interesting finding is that the imidacloprid resistant populations of N. lugens showed little cross-resistance to these potential neonicotinoids with a -NO 2 or -CN group in trans-configuration. 33,34) Among these potential neonicotinoids, the dicyclic neonicotinoids with cis-configuration discriminated between the highand low-affinity imidacloprid-binding sites in N. lugens and their potencies were only slightly influenced by the previously identified mutation Y151S in N. lugens.…”

Crystal Structure of 8-(6-Chloro-pyridin-3-ylmethyl)-2,6,7,8-tetrahydroimidazo[2,1-c][1,2,6-chloropyridyl-3-yl-4] triazin-3-one

“…1 Neonicotinoidsareasetofnicotine-basedinsecticide that include the chemicals imidacloprid, clothianidin, acetamiprid, thiacloprid, thiamethoxam, dinotefuran and nitenpyram; they possess either nitromethylene, nitroimine or cyanoimine groups. 2,3 The neonicotinoids has close affinity towardsinsectnAChRs,whichsuggeststhatnAChRsarelikely to represent the principal site of action of these compounds. 4,5 Neonicotinoids are highly effective, and the largest selling insecticide worldwide for crop protection and veterinary pest control.…”

QSAR Study of Neonicotinoid Insecticidal Activity Against Cowpea Aphids by the MLR approach

“…A set of 30 neonicotinoid analogues bearing nitroconjugated double bond and five-membered heterocycles and nitromethylene neonicotinoids containing a tetrahydropyridine ring with exo-ring ether modifications with known insecticidal activity was analyzed [6,7]. The insecticidal activity against cowpea aphids (Aphis craccivora) activity data, expressed as pLC 50 values (where LC 50 represents the median lethal concentration of the chemical in air that kills 50% of the test animals during the observation period) was used as dependent variable.…”