Kevin G. Meyer

Corteva (United States)

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Co-Authors

Chenglin Yao

Corteva (United States)

David R. Williams

Indiana University Bloomington

Nick X. Wang

Corteva (United States)

Thomas J Slanec

Corteva (United States)

W. J. Owen

Corteva (United States)

Jessica Herrick

University of Illinois Chicago

Richard B. Rogers

Glenn Research Center

Karla Bravo‐Altamirano

Pfizer (United States)

Jeremy T. Wilmot

Corteva (United States)

Dawn A. Brooks

Eli Lilly (United States)

Cooperative Institutions

Corteva (United States)

Syngenta (Switzerland)

FMC (United States)

BASF (United States)

BASF (Germany)

Indianapolis Zoo

East China University of Science and Technology

Syngenta (United Kingdom)

DuPont (United States)

Chinese Academy of Sciences

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Diastereoselectivity in Asymmetric Allylations: The Role of Vicinal Chirality in the Allyl Nucleophile for S_E2′ Reactions with Aldehydes.

ChemInform (2004)

David R. Williams Kevin G. Meyer Khalida Shamim Samarjit Patnaik

Abstract For Abstract see ChemInform Abstract in Full Text.

Vicinal

Chirality

10.1002/chin.200433031

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Citations (0)

Synthesis and biological activity of analogs of the antifungal antibiotic UK‐2A. III. Impact of modifications to the macrocycle isobutyryl ester position

Pest Management Science (2019)

W. J. Owen Kevin G. Meyer Thomas J Slanec Stacy T Meyer Nick X. Wang

Abstract BACKGROUND Fenpicoxamid (Inatreq™ active), a new fungicide under development by Corteva Agriscience™, Agriculture Division of DowDuPont, is an isobutyryl acetal derivative of the antifungal antibiotic UK‐2A. SAR studies around the picolinamide ring and benzyl substituents attached at positions 3 and 8, respectively, of the UK‐2A bislactone macrocycle have recently been documented. This study focuses on replacement of the isobutyryl ester group in the 7 position. RESULTS Thirty analogs, predominantly esters and ethers, were prepared and evaluated for inhibition of mitochondrial electron transport and in vitro growth of Zymoseptoria tritici , Leptosphaeria nodorum , Pyricularia oryzae and Ustilago maydis . Aliphatic substituents containing four to six carbon atoms deliver strong intrinsic activity, the pivaloate ester (IC 50 1.44 nM) and the n ‐butyl, 1‐Me‐propyl, 3,3‐diMe‐propyl and 2‐ c ‐propyl propyl ethers (IC 50 values = 1.08, 1.14, 1.15 & 1.32 nM, respectively) being the most active derivatives. QSAR modelling identified solvation energy ( E solv ) and critical packing parameters ( vsurf_CP ) as highly significant molecular descriptors for explaining relative intrinsic activity of analogs. Activity translation to fungal growth inhibition and disease control testing was significantly influenced by intrinsic activity and physical properties, the cyclopropanecarboxylate ester (log D 3.67, IC 50 3.36 nM, Z. tritici EC 50 12 μg L −1 ) showing the strongest Z. tritici activity in protectant tests. CONCLUSIONS Substitution of the isobutyryl ester group of UK‐2A generates analogs that retain strong antifungal activity against Z. tritici and other fungi. © 2019 Society of Chemical Industry

Pyricularia

Ustilago

10.1002/ps.5511

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Citations (15)

ChemInform Abstract: Palladium‐Induced Cyclizations for the Synthesis of cis‐2,5‐Disubstituted‐3‐methylenetetrahydrofurans: Studies of the C₇—C₂₂ Core of Amphidinolide K.

ChemInform (2000)

David R. Williams Kevin G. Meyer

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

10.1002/chin.200004121

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ChemInform Abstract: Asymmetric Allylation. An Effective Strategy for the Convergent Synthesis of Highly Functionalized Homoallylic Alcohols

ChemInform (1999)

David R. Williams Dawn A. Brooks Kevin G. Meyer Michael P. Clark

Convergent synthesis

10.1002/chin.199901261

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Simple Preparation of Monoalkylhydrazines (IV).

ChemInform (2005)

Kevin G. Meyer

10.1002/chin.200517069

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Cover Image, Volume 75, Issue 9

Pest Management Science (2019)

Beth A. Lorsbach Thomas C. Sparks Robert M. Cicchillo Negar V Garizi Donald R. Hahn

The cover image is based on the Perspective Natural Products: A Strategic Lead Generation Approach in Crop Protection Discovery by Beth A Lorsbach et al., https://doi.org/10.1002/ps.5350 . image

10.1002/ps.5571

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Citations (11)

Asymmetric allylation. An effective strategy for the convergent synthesis of highly functionalized homoallylic alcohols

Tetrahedron Letters (1998)

David R. Williams Dawn A. Brooks Kevin G. Meyer Michael P. Clark

Transmetalation

Stannane

Boranes

Convergent synthesis

10.1016/s0040-4039(98)01557-3

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Citations (40)

Florylpicoxamid, a new picolinamide fungicide with broad spectrum activity

Pest Management Science (2021)

Chenglin Yao Kevin G. Meyer Courtney Gallup Andrew J. Bowling Andrea Hufnagl

Abstract BACKGROUND Following the introduction of fenpicoxamid, a natural product‐based fungicide targeting the Qi site of mitochondrial cytochrome bc1 complex, a second generation fully synthetic picolinamide, florylpicoxamid, was discovered and its biological activity and attributes were characterized. RESULTS In vitro fungal growth inhibition assays and in planta glasshouse biological activity evaluations showed florylpicoxamid was active against 21 different plant pathogenic fungi within the phyla Ascomycota and Basidiomycota. Among the pathogens evaluated, florylpicoxamid was most potent against Zymoseptoria tritici , the causal organism of wheat leaf blotch, providing 80% growth inhibition in vitro at 0.0046 mg L −1 and 80% disease control in planta at 0.03 mg L −1 when applied as a preventative treatment. Florylpicoxamid was more efficacious than epoxiconazole, fluxapyroxad, and benzovindiflupyr versus a Z. tritici wild‐type isolate when applied as curative and preventative treatments, with superior 10‐day curative reachback activity. Analytical studies and in planta tests demonstrated that florylpicoxamid partitioned into plants quickly and showed good systemicity and translaminar activity on both monocot and dicot plants. No cross‐resistance was observed between florylpicoxamid and strobilurin or azole fungicides. Florylpicoxamid exerts its preventative effect by preventing spore germination on the leaf surface and curative activity by arresting mycelial growth and pycnidia development in leaf tissue. CONCLUSIONS With strong broad spectrum fungicidal activity, florylpicoxamid delivers an innovative solution for growers to sustain high productivity and quality of many crops, and also provides a new option for developing effective strategies for fungicide resistance management. © 2021 Society of Chemical Industry.

Strobilurin

Spore germination

Broad spectrum

Tebuconazole

10.1002/ps.6483

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Citations (26)

Palladium-Induced Cyclizations for the Synthesis of cis-2,5-Disubstituted-3- methylenetetrahydrofurans: Studies of the C₇−C₂₂ Core of Amphidinolide K

Organic Letters (1999)

David R. Williams Kevin G. Meyer

The diastereoselective synthesis of cis-2,5-disubstituted-3-methylenetetrahydrofurans via Pd(0)-catalyzed cyclization of 2-methylene-1,4-diols is described. Investigations into the scope of the reaction and its application toward the synthesis of amphidinolide K is reported.

Methylene

Scope (computer science)

10.1021/ol990255l

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Citations (24)

Total Synthesis of Amphidinolide K, a Macrolide That Stabilizes F-Actin

The Journal of Organic Chemistry (2015)

Dani Sánchez Thanos Andreou Anna M. Costa Kevin G. Meyer David R. Williams

The total synthesis of (-)-amphidinolide K (1) based on asymmetric addition of allylsilane C1-C8 to enal C9-C22 is reported. The 1,9,18-tris-O-TBDPS ether was converted into the desired 9,18-dihydroxy acid. Its macrolactonization was accomplished by the Shiina method. Compound 1 together with some of its stereoisomers and analogues were subjected to evaluation of the possible disruption of the α,β-tubulin-microtubule and/or G-actin-F-actin equilibria. Compound 1 behaves as a stabilizer of actin filaments (F-actin) in vitro.

10.1021/acs.joc.5b00966

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Citations (15)