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

被引：15

作者：

Dent, William H., III ^{[1
]}

Pobanz, Mark A. ^{[1
]}

Geng, Chaoxian ^{[1
]}

Sparks, Thomas C. ^{[1
]}

Watson, Gerald B. ^{[1
]}

Letherer, Theodore J. ^{[1
]}

Beavers, Kenneth W. ^{[1
]}

Young, Cathy D. ^{[1
]}

Adelfinskaya, Yelena A. ^{[1
]}

Ross, Ronald R. ^{[1
]}

Whiteker, Greg ^{[1
]}

Renga, James ^{[1
]}

机构：

[1] Dow AgroSci, 9330 Zionsville Rd, Indianapolis, IN 46268 USA

来源：

PEST MANAGEMENT SCIENCE | 2017年 / 73卷 / 04期

关键词：

GABA antagonism; insecticidal activity; pyrazolopyridine; pyrazolopyrimidine; investigational biology;

D O I：

10.1002/ps.4431

中图分类号：

S3 [农学（农艺学）];

学科分类号：

0901 ;

摘要：

BACKGROUND-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. RESULTSThrough >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. CONCLUSIONAn 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. (c) 2016 Society of Chemical Industry

引用

页码：774 / 781

页数：8

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