Discovery of oxathiapiprolin, a new oomycete fungicide that targets an oxysterol binding protein

Pasteris, Robert J.; Hanagan, Mary Ann; Bisaha, John J.; Finkelstein, Bruce L.; Hoffman, Lisa E.; Gregory, Vann; Andreassi, John L.; Sweigard, James A.; Klyashchitsky, Boris A.; Henry, Yewande T.; Berger, Richard A.

doi:10.1016/j.bmc.2015.07.064

Cited by 145 publications

(162 citation statements)

References 4 publications

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“…), is the first member of a novel class of piperidinyl thiazole isoxazoline fungicides with exceptionally high activity against diseases caused by Oomycete pathogens. Via a novel target for fungicides, it inhibits an oxysterol‐binding protein resulting in excellent preventive, curative and residual efficacy against diseases in grapes, potatoes and vegetables at low use rates …”

Section: Fungicidesmentioning

confidence: 99%

Current status of chirality in agrochemicals

Jeschke

2018

Pest Management Science

148

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The agrochemical industry is searching continuously for new pesticides to develop products that have optimal efficacy, lower application rates in the field, increased selectivity, favourable toxicological and environmental safety, enhanced user friendliness and better economic viability. One strategy by which to achieve these ambitious goals makes use of the unique properties of molecules containing asymmetric centres. In the past, many natural products and their congeners have been a source of inspiration in the design of new active ingredients, and the molecular structures of the resulting compounds have become increasingly complex; some 30% contain fragments with asymmetric centres. However, despite enormous progress in catalytic asymmetric processes over the past decade, few agrochemicals are produced in an enantiomerically pure or enriched form on an industrial scale. Since 2007, ∼ 43% of the 44 products launched (insecticides, acaricides, fungicides, nematicides and herbicides) contain one or more asymmetric centres in the molecule (∼ 47%) and most have been launched as racemic mixtures of enantiomers or diastereomers. This review provides an overview of the current status of chiral agrochemicals launched over the past 10 years and describes the inherently connected challenges of modern agricultural chemistry by managing important aspects resulting from the stereochemistry of these innovative products. © 2018 Society of Chemical Industry.

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Section: Fungicidesmentioning

confidence: 99%

Current status of chirality in agrochemicals

Jeschke

2018

Pest Management Science

148

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“…This enzyme, also known as CYP51, is part of the fungal sterol biosynthesis pathway from the acyclic terpenoid squalene to the tetracyclic ergosterol. The currently most recent and efficacious solution against the already mentioned Oomycete diseases potato late blight and grape downy mildew is the isoxazoline derivative oxathiapiprolin ( 20 ), which introduced a completely new mode of action to the fungicide market, namely, the inhibition of an oxysterol‐binding protein . Finally, the very simple isoxazole derivative hymexazol ( 21 ) is specialized on the control of soil‐borne diseases caused by Fusarium and Pythium spp.…”

Section: Oxazole‐based and Isoxzole‐based Market And Developmental Prmentioning

confidence: 99%

Oxazole and Isoxazole Chemistry in Crop Protection

Lamberth

2018

Journal of Heterocyclic Chem

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An overview is given of the significance of the oxazole and isoxazole scaffolds in crop protection chemistry. The main herbicidally, fungicidally, and insecticidally active oxazole and isoxazole classes are presented, together with their synthesis routes, modes of action, and biological efficacies. In addition, the role of oxazoles and isoxazoles as lead structure or as intermediate in the synthesis of other agrochemicals is reported. Also, partially and fully saturated oxazole and isoxazole derivatives such as oxazolines, isoxazolines, oxazolidines, and isoxazolidines, oxygenated derivatives such as oxazolones and isoxazolones as well as annulated derivatives, such as benzoxazoles and benzisoxazoles, are covered.

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“…Another approach toward the discovery of novel insecticidal compounds is to employ high‐throughput screening of diverse or structurally focused sets of chemistry for activity against insect pests . The availability of commercial compound collections makes this approach an attractive one.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological activity of pyridazine amides, hydrazones and hydrazides

Buysse¹,

Yap²,

Hunter³

et al. 2017

Pest Management Science

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A series of aphicidal [6-(3-pyridyl)pyridazin-3-yl]amides were discovered as a result of random screening of compounds that were intially investigated as herbicides. Follow-up studies of the structure-activity relationship of these [6-(3-pyridyl)pyridazin-3-yl]amides showed that biosteric replacement of the amide moiety was widely tolerated suggesting that further opportunities for exploitation may exist for this new area of insecticidal chemistry. Insecticidal efficacy from the original hit, compound 1, to the efficacy of compound 14 produced greater than 10-fold potency improvement against Aphis gossypii and greater than 14-fold potency improvement against Myzus persicae. © 2016 Society of Chemical Industry.

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Discovery of oxathiapiprolin, a new oomycete fungicide that targets an oxysterol binding protein

Cited by 145 publications

References 4 publications

Current status of chirality in agrochemicals

Current status of chirality in agrochemicals

Oxazole and Isoxazole Chemistry in Crop Protection

Synthesis and biological activity of pyridazine amides, hydrazones and hydrazides

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