Synthesis and biological activity of a novel insecticide, benzpyrimoxan

Satoh, Eikoh; Kasahara, Ryota; Fukatsu, K.; Aoki, Takao; Harayama, Hiroto; Murata, Tetsuya; Suwa, Akiyuki

doi:10.1016/b978-0-12-821035-2.00014-0

Cited by 3 publications

(2 citation statements)

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“…19). 100 It was found that replacement of alkoxy or alkyl groups with a longer chain than the methoxy, sec-butoxy or n-butyl group can result in high insecticidal activity. Based on a cyclohexyl group as substituent, the introduction of an oxygen atom into this ring system resulted in improved residual efficacy.…”

Section: Benzpyrimoxanmentioning

confidence: 99%

Recent developments in fluorine‐containing pesticides

Jeschke

2024

Pest Management Science

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To ensure ongoing sustainability, the modern agrochemical industry is faced with enormous challenges. These arise from provision of high‐quality food to increasing water use and environmental impact as well as growing world population. The loss of previous agrochemicals due to consumer perception, changing grower needs and everchanging regulatory requirements is higher than the number of active ingredients can being introduced into the crop protection market. Therefore, the development of novel agrochemicals is essential, that can provide improved efficacy and environmental profiles. In this context, introduction of fluorine atoms and fluorine‐containing motifs into a molecule is an important method to influence its physicochemical properties. These include for example small difluoro‐ and trifluoromethyl, or trifluoromethoxy groups at aryl or heterocyclic aryl moieties but also fragments like 2,2,2‐trifluoroethoxycarbonyl, trifluoromethylsulfonyl, trifluoroacetyl, as well as the so far unusal rest like heptafluoro‐iso‐propyl. This review gives an overview of recent developments of fluorine‐containing pesticides launched over the past 7 years and describes a selection of current fluorine‐containing development candidates.This article is protected by copyright. All rights reserved.

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Section: Benzpyrimoxanmentioning

confidence: 99%

Recent developments in fluorine‐containing pesticides

Jeschke

2024

Pest Management Science

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“…The incorporation of flexible linkers as a scaffold-hopping strategy has been successfully employed in the insecticide space. The elongation of the oxygen spacer in the pyridyloxyphenyl derivative 40 to a 1,3-dioxypropyl bridge led to the discovery of pyridalyl ( 41 ), which shows excellent control of different lepidopterous and thysanopterous pests. , Inserting a OCH 2 linker between the phenyl and pyrimidinyl rings of the lead compound 42 delivered the novel insecticide benzpyrimoxan ( 43 ), which shows good activity against nymphs of Nilaparvata lugens (brown plant hopper) . The oxazoline derivative 45 bears an additional acetylene linker compared to its lead compound 44 .…”

Section: Further Insertion Examples Involving Other Mode Of Action Cl...mentioning

confidence: 99%

Insertion of Small Flexible Linkers as a Useful Scaffold Hopping Tool in Agrochemistry

Lamberth

2022

J. Agric. Food Chem.

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Inserting small flexible linkers of only one- to three-atom chain lengths into a molecular backbone is an important scaffold hopping manipulation. Analogues derived from biologically active compounds through the utilization of such a strategy are often similar in shape and physicochemical properties and, therefore, likely to exhibit similar potency. This review will demonstrate how the elongation with oxygen, amino, methylene, ethylene, vinyl, ethynyl, and CH2O bridges led to the discovery of highly active agrochemicals.

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Innovation in insecticide discovery: Approaches to the discovery of new classes of insecticides

Sparks¹,

Bryant

2022

Pest Management Science

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The continuing demand for agrochemical insecticides that can meet increasing grower, environmental, consumer and regulatory requirements creates the need for the development of new solutions for managing crop pest insects. The development of resistance to the currently available insecticidal products adds another critical driver for new insecticidal active ingredients (AIs). One avenue to meeting these challenges is the creation of new classes of insecticidal molecules to act as starting points and prototypes stimulating further spectrum, efficacy and environmental impact refinements. A new class of insecticides is foreshadowed by the first molecule exemplifying that class (first‐in‐class, FIC) and offers one measure of innovation within the agrochemical industry. Most insecticides owe their discovery to competitor‐inspired (i.e. competitor patents/products) or next‐generation (follow‐on to a company's pre‐existing product) strategies. In contrast, FIC insecticides primarily emerge from a bioactive hypothesis approach, with the largest segment resulting from the exploration of new areas of chemistry/heterocycles and underexploited motifs. Natural products also play an important role in the discovery of FIC insecticides. Understanding the origins of these FIC compounds and the approaches used in their discovery can provide insights into successful strategies for future FIC insecticides. This review analyses information on historic and recently introduced FIC insecticides. Its main objective has been to identify the most successful discovery strategies for identifying new agrochemical solutions to meet the challenge of minimizing crop losses resulting from insects. © 2022 Society of Chemical Industry.

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Synthesis and biological activity of a novel insecticide, benzpyrimoxan

Cited by 3 publications

References 1 publication

Recent developments in fluorine‐containing pesticides

Recent developments in fluorine‐containing pesticides

Insertion of Small Flexible Linkers as a Useful Scaffold Hopping Tool in Agrochemistry

Innovation in insecticide discovery: Approaches to the discovery of new classes of insecticides

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