Oxathiapiprolin | CAS# 1003318-67-9 | Oomycete Fungicide

MedKoo Cat#: 565077 | Name: Oxathiapiprolin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oxathiapiprolin is a oomycete fungicide, targeting an oxysterol binding protein.

Chemical Structure

Oxathiapiprolin

CAS#1003318-67-9

Theoretical Analysis

MedKoo Cat#: 565077

Name: Oxathiapiprolin

CAS#: 1003318-67-9

Chemical Formula: C24H22F5N5O2S

Exact Mass: 539.1414

Molecular Weight: 539.53

Elemental Analysis: C, 53.43; H, 4.11; F, 17.61; N, 12.98; O, 5.93; S, 5.94

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Synonym

Oxathiapiprolin;

IUPAC/Chemical Name

1-[4-[4-[5-(2,6-Difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]ethanone

InChi Key

IAQLCKZJGNTRDO-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H22F5N5O2S/c1-13-9-20(24(27,28)29)31-34(13)11-21(35)33-7-5-14(6-8-33)23-30-18(12-37-23)17-10-19(36-32-17)22-15(25)3-2-4-16(22)26/h2-4,9,12,14,19H,5-8,10-11H2,1H3

SMILES Code

FC(C1=NN(CC(N2CCC(C3=NC(C4=NOC(C5=C(F)C=CC=C5F)C4)=CS3)CC2)=O)C(C)=C1)(F)F

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oxathiapiprolin is a oomycete fungicide.

In vitro activity:

Oxathiapiprolin was found to change the structure of soil fungal communities, among which Ascomycota and Mortierellomycota were the most affected. Undefined saprophytic fungi increased in the treatment groups, and the colonization of saprophytic fungi can act as a major contributor to the function of soil microbial communities. Reference: Toxics. 2022 Sep 19;10(9):548. https://pubmed.ncbi.nlm.nih.gov/36136513/

In vivo activity:

This study investigated the potential and related mechanism of oxathiapiprolin to activate the plant disease resistance using the bacterium Pseudomonas syringae pv tomato (Pst) and plant Arabidopsis interaction as the targeted system. Results showed that oxathiapiprolin could activate the plant disease resistance against Pst DC3000, a non-target pathogen of oxathiapiprolin, in Arabidopsis, tobacco, and tomato plants. Reference: Int J Mol Sci. 2020 Feb 12;21(4):1223. https://pubmed.ncbi.nlm.nih.gov/32059380/

Preparing Stock Solutions

The following data is based on the product molecular weight 539.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Chen Y, Zhang F, Huang B, Wang J, Huang H, Song Z, Nong S, Huang C, Wei J, Jia H. Effects of Oxathiapiprolin on the Structure, Diversity and Function of Soil Fungal Community. Toxics. 2022 Sep 19;10(9):548. doi: 10.3390/toxics10090548. PMID: 36136513; PMCID: PMC9504812. 2. Peng Q, Wang Z, Liu P, Liang Y, Zhao Z, Li W, Liu X, Xia Y. Oxathiapiprolin, a Novel Chemical Inducer Activates the Plant Disease Resistance. Int J Mol Sci. 2020 Feb 12;21(4):1223. doi: 10.3390/ijms21041223. PMID: 32059380; PMCID: PMC7072870. 3. Cohen Y. The Novel Oomycide Oxathiapiprolin Inhibits All Stages in the Asexual Life Cycle of Pseudoperonospora cubensis - Causal Agent of Cucurbit Downy Mildew. PLoS One. 2015 Oct 9;10(10):e0140015. doi: 10.1371/journal.pone.0140015. PMID: 26452052; PMCID: PMC4599937.

In vitro protocol:

In vivo protocol:

1. Peng Q, Wang Z, Liu P, Liang Y, Zhao Z, Li W, Liu X, Xia Y. Oxathiapiprolin, a Novel Chemical Inducer Activates the Plant Disease Resistance. Int J Mol Sci. 2020 Feb 12;21(4):1223. doi: 10.3390/ijms21041223. PMID: 32059380; PMCID: PMC7072870. 2. Cohen Y. The Novel Oomycide Oxathiapiprolin Inhibits All Stages in the Asexual Life Cycle of Pseudoperonospora cubensis - Causal Agent of Cucurbit Downy Mildew. PLoS One. 2015 Oct 9;10(10):e0140015. doi: 10.1371/journal.pone.0140015. PMID: 26452052; PMCID: PMC4599937.

1: Cohen Y, Rubin AE, Galperin M. Oxathiapiprolin-based fungicides provide enhanced control of tomato late blight induced by mefenoxam-insensitive Phytophthora infestans. PLoS One. 2018 Sep 27;13(9):e0204523. doi: 10.1371/journal.pone.0204523. eCollection 2018. PubMed PMID: 30260986; PubMed Central PMCID: PMC6160094. 2: Feng X, Wang K, Pan L, Xu T, Zhang H, Fantke P. Measured and Modeled Residue Dynamics of Famoxadone and Oxathiapiprolin in Tomato Fields. J Agric Food Chem. 2018 Aug 15;66(32):8489-8495. doi: 10.1021/acs.jafc.8b02056. Epub 2018 Aug 1. PubMed PMID: 30028951. 3: Miao J, Chi Y, Lin D, Tyler BM, Liu X. Mutations in ORP1 Conferring Oxathiapiprolin Resistance Confirmed by Genome Editing using CRISPR/Cas9 in Phytophthora capsici and P. sojae. Phytopathology. 2018 Dec;108(12):1412-1419. doi: 10.1094/PHYTO-01-18-0010-R. Epub 2018 Oct 31. PubMed PMID: 29979095. 4: Miao J, Dong X, Chi Y, Lin D, Chen F, Du Y, Liu P, Liu X. Pseudoperonospora cubensis in China: Its sensitivity to and control by oxathiapiprolin. Pestic Biochem Physiol. 2018 May;147:96-101. doi: 10.1016/j.pestbp.2018.03.009. Epub 2018 Mar 27. PubMed PMID: 29933999. 5: Huang C, Xu H, Zhang D, Tan C, Pan Y, Wang S, Qian H, Ying Y, Gadd GM, Pan X. TEMPORARY REMOVAL: Effects of oxathiapiprolin on photosynthetic activity of Chlorella pyrenoidosa probed by chlorophyll fluorescence and thermoluminescence assays. Pestic Biochem Physiol. 2017 Oct;142:161. doi: 10.1016/j.pestbp.2017.07.004. Epub 2017 Jul 13. PubMed PMID: 29107241. 6: Yu P, Jia C, Zhao E, Chen L, He H, Jing J, He M. Determination of oxathiapiprolin concentration and dissipation in grapes and soil by ultrahigh-performance liquid chromatography-tandem mass spectrometry. J Sci Food Agric. 2017 Aug;97(10):3294-3299. doi: 10.1002/jsfa.8178. Epub 2017 Feb 8. PubMed PMID: 27976410. 7: Qu T, Shao Y, Csinos AS, Ji P. Sensitivity of Phytophthora nicotianae From Tobacco to Fluopicolide, Mandipropamid, and Oxathiapiprolin. Plant Dis. 2016 Oct;100(10):2119-2125. doi: 10.1094/PDIS-04-16-0429-RE. Epub 2016 Jul 18. PubMed PMID: 30683015. 8: Qu T, Grey TL, Csinos AS, Ji P. Translocation of Oxathiapiprolin in Bell Pepper Plants and Systemic Protection of Plants Against Phytophthora Blight. Plant Dis. 2016 Sep;100(9):1931-1936. doi: 10.1094/PDIS-03-16-0370-RE. Epub 2016 Jun 30. PubMed PMID: 30682987. 9: Miao J, Cai M, Dong X, Liu L, Lin D, Zhang C, Pang Z, Liu X. Resistance Assessment for Oxathiapiprolin in Phytophthora capsici and the Detection of a Point Mutation (G769W) in PcORP1 that Confers Resistance. Front Microbiol. 2016 Apr 29;7:615. doi: 10.3389/fmicb.2016.00615. eCollection 2016. PubMed PMID: 27199944; PubMed Central PMCID: PMC4850160. 10: Miao J, Dong X, Lin D, Wang Q, Liu P, Chen F, Du Y, Liu X. Activity of the novel fungicide oxathiapiprolin against plant-pathogenic oomycetes. Pest Manag Sci. 2016 Aug;72(8):1572-7. doi: 10.1002/ps.4189. Epub 2015 Dec 21. PubMed PMID: 26577849. 11: Cohen Y. The Novel Oomycide Oxathiapiprolin Inhibits All Stages in the Asexual Life Cycle of Pseudoperonospora cubensis - Causal Agent of Cucurbit Downy Mildew. PLoS One. 2015 Oct 9;10(10):e0140015. doi: 10.1371/journal.pone.0140015. eCollection 2015. PubMed PMID: 26452052; PubMed Central PMCID: PMC4599937. 12: Pasteris RJ, Hanagan MA, Bisaha JJ, Finkelstein BL, Hoffman LE, Gregory V, Andreassi JL, Sweigard JA, Klyashchitsky BA, Henry YT, Berger RA. Discovery of oxathiapiprolin, a new oomycete fungicide that targets an oxysterol binding protein. Bioorg Med Chem. 2016 Feb 1;24(3):354-61. doi: 10.1016/j.bmc.2015.07.064. Epub 2015 Jul 31. PubMed PMID: 26314923. 13: Ju C, Dong F, Liu X, Wu X, Zhao H, Zheng Y, Xu J. Rapid residue analysis of oxathiapiprolin and its metabolites in typical Chinese soil, water, and sediments by a modified quick, easy, cheap, effective, rugged, and safe method with ultra high performance liquid chromatography and tandem mass spectrometry. J Sep Sci. 2015 Mar;38(6):909-16. doi: 10.1002/jssc.201401126. Epub 2015 Feb 12. PubMed PMID: 25581592. 14: Ji P, Csinos AS, Hickman LL, Hargett U. Efficacy and Application Methods of Oxathiapiprolin for Management of Black Shank on Tobacco. Plant Dis. 2014 Nov;98(11):1551-1554. doi: 10.1094/PDIS-02-14-0172-RE. PubMed PMID: 30699789. 15: Wu X, Xu J, Dong F, Liu X, Li Y, Zheng Y. Simultaneous determination of oxathiapiprolin and two metabolites in fruits, vegetables and cereal using a modified quick, easy, cheap, effective, rugged, and safe method and liquid chromatography coupled to tandem mass spectrometry. J Chromatogr A. 2014 Feb 14;1329:30-7. doi: 10.1016/j.chroma.2013.12.087. Epub 2014 Jan 8. PubMed PMID: 24440097.