Synthesis and Insecticidal Activity of New 2-Aryl-3,5-dihydro-2H-1,4-Benzoxazepine Derivatives

Cassayre, Jérôme; Hüter, Ottmar; Hughes, D. L.; O'Sullivan, Anthony C.; Craig, Wayne; Jacob, Olivier; Clarke, Eric D.; Earley, Fergus G.P.; Schade, Anja

doi:10.1021/bk-2015-1204.ch028

Cited by 3 publications

(3 citation statements)

References 21 publications

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“…The present study aims to provide experimental evidence for the postulated vacuole trapping of basic pesticides in leaf cells. 10,11,34 The accumulation of weakly basic compounds in acidic organelles has been observed in animal and human cells 12,17,46,51 and was also recently discovered for acidic vesicles of protozoa. 20 Ion trapping of weakly acidic herbicides leads to phloem transport and systemic translocation in plants 27,48 and is well described for phytohormones such as auxins 21,35 and abscisic acid.…”

Section: ■ Introductionmentioning

confidence: 83%

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How To Design for a Tailored Subcellular Distribution of Systemic Agrochemicals in Plant Tissues

Hofstetter

Beck

Trapp

et al. 2018

J. Agric. Food Chem.

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Foliar-applied systemic agrochemicals require entrance into the plant vascular system or into specific subcellular compartments to reach their target in planta or to be imbibed by piercing/sucking pests. An inappropriate subcellular localization, like accumulation of aphicides in vacuoles, might lower the compound's efficiency due to reduced exposure to the target. Permeabilities and mass distributions of 16 compounds covering a broad range of properties were measured across a pH gradient in a PAMPA ("parallel artificial membrane permeability assay") system, providing experimental evidence for ion trapping of acids and bases in basic and acidic compartments, respectively. The results validated a predictive model which was then expanded to simulate a standardized plant cell (cytosol and vacuole) with a vascular system (phloem and xylem). This approach underlined that the absolute mass distribution across aqueous phases is defined by membrane retention, whereas the relative mass distribution is determined by the species (neutral, acidic, basic) of compounds. These processes depend largely on p K and log K of the test compounds, which subsequently determine the partitioning of the substances in plant cell compartments. The validated model can be used as a tool in agrochemistry research to tailor the subcellular distribution by chemistry design and to interpret biology results.

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Section: ■ Introductionmentioning

confidence: 83%

“…The present study aims to provide experimental evidence for the postulated vacuole trapping of basic pesticides in leaf cells. ,, …”

Section: Introductionmentioning

confidence: 99%

How To Design for a Tailored Subcellular Distribution of Systemic Agrochemicals in Plant Tissues

Hofstetter

Beck

Trapp

et al. 2018

J. Agric. Food Chem.

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show abstract

“…In the final step, the transition-metal catalyzed replacement of the bromine atom by a cyano group affords the experimental insecticide 127, which is, as well as 126, active against sucking pests, such as aphids and whiteflies (Scheme 9). 103…”

Section: Miscellaneous Modes Of Actionmentioning

confidence: 99%

Imidazole Chemistry in Crop Protection

Lamberth¹

2021

HETEROCYCLES

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An overview is given of the significance of the imidazole scaffold in crop protection chemistry. The main herbicidally, fungicidally and insecticidally active imidazole classes are presented, together with their synthesis routes, modes of action and biological efficacies. Also, partially and fully saturated imidazole derivatives, such as imidazolines and imidazolidines, oxygenated derivatives, such as imidazolinones and hydantoins as well as annulated derivatives, such as benzimidazoles, are covered. In addition, also the role of imidazoles as intermediates or reagents in the synthesis of other agrochemicals is reported. CONTENTS 1. Introduction 2. Herbicidally active imidazole derivatives 2.1. Acetohydroxyacid synthase inhibitors 2.2. Protoporphyrinogen-IX-oxidase inhibitors 2.3. Miscellaneous modes of action 2.4. Natural products 3. Fungicidally active imidazole derivatives 3.1. C14-demethylase inhibitors 3.2. Tubulin polymerization inhibitors and promoters 3.3. Miscellaneous modes of action 3.4. Natural products 4. Insecticidally active imidazole derivatives 4.1. Nicotinic acetylcholine receptor agonists 4.2. Miscellaneous modes of action 4.3. Natural products 5. Imidazoles as reagents and intermediates in the synthesis of non-imidazole agrochemicals 6. Conclusion

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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 Insecticidal Activity of New 2-Aryl-3,5-dihydro-2H-1,4-Benzoxazepine Derivatives

Cited by 3 publications

References 21 publications

How To Design for a Tailored Subcellular Distribution of Systemic Agrochemicals in Plant Tissues

How To Design for a Tailored Subcellular Distribution of Systemic Agrochemicals in Plant Tissues

Imidazole Chemistry in Crop Protection

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

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