Discovery of the aryl heterocyclic amine insecticides: synthesis, insecticidal activity, field results, mode of action and bioavailability of a leading field candidate.

Autor: Dent WH 3rd; Dow AgroSciences, Indianapolis, IN, USA., Pobanz MA; Dow AgroSciences, Indianapolis, IN, USA., Geng C; Dow AgroSciences, Indianapolis, IN, USA., Sparks TC; Dow AgroSciences, Indianapolis, IN, USA., Watson GB; Dow AgroSciences, Indianapolis, IN, USA., Letherer TJ; Dow AgroSciences, Indianapolis, IN, USA., Beavers KW; Dow AgroSciences, Indianapolis, IN, USA., Young CD; Dow AgroSciences, Indianapolis, IN, USA., Adelfinskaya YA; Dow AgroSciences, Indianapolis, IN, USA., Ross RR; Dow AgroSciences, Indianapolis, IN, USA., Whiteker G; Dow AgroSciences, Indianapolis, IN, USA., Renga J; Dow AgroSciences, Indianapolis, IN, USA.
Jazyk: angličtina
Zdroj: Pest management science [Pest Manag Sci] 2017 Apr; Vol. 73 (4), pp. 774-781. Date of Electronic Publication: 2016 Oct 26.
DOI: 10.1002/ps.4431
Abstrakt: Background: γ-Amino butyric acid (GABA) antagonists are proven targets for control of lepidopteran and other pests. New heterocyclic compounds with high insecticidal activity were discovered using a competitive-intelligence-inspired scaffold-hopping approach to generate analogs of fipronil, a known GABA antagonist. These novel aryl heterocyclic amines (AHAs) displayed broad-spectrum activity on a number of chewing insect pests.
Results: Through >370 modifications of the core AHA structure, a 7-pyrazolopyridine lead molecule was found to exhibit much improved activity on a number of insect pests. In field trial studies, its performance was 2-4 times lower than commercial standards and also appeared to be species dependent, with good activity seen for larvae of Spodoptera exigua, but inactivity on larvae of Trichoplusia ni.
Conclusion: An extensive investigational biology effort demonstrated that these AHA analogs appear to have multiple modes of action, including GABA receptor antagonism and mitopotential or uncoupler activity. The limited capability in larvae of T. ni to convert the lead molecule to its associated open form correlates with the low toxicity of the lead molecule in this species. This work has provided information that could aid investigations of novel GABA antagonists. © 2016 Society of Chemical Industry.
(© 2016 Society of Chemical Industry.)
Databáze: MEDLINE
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