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MedKoo Cat#: 146273 | Name: Probenazole

Description:

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

Probenazole is a plant defense activator used primarily in agriculture to enhance disease resistance in crops such as rice, vegetables, and fruits. It does not act directly on pathogens but instead stimulates the plant's innate immune system, particularly by inducing systemic acquired resistance (SAR). This activation leads to the production of pathogenesis-related proteins and other defense compounds that help the plant resist infections from fungi, bacteria, and viruses. Probenazole is especially effective against diseases like rice blast and bacterial leaf blight.

Chemical Structure

Probenazole
Probenazole
CAS#27605-76-1

Theoretical Analysis

MedKoo Cat#: 146273

Name: Probenazole

CAS#: 27605-76-1

Chemical Formula: C10H9NO3S

Exact Mass: 223.0303

Molecular Weight: 223.25

Elemental Analysis: C, 53.80; H, 4.06; N, 6.27; O, 21.50; S, 14.36

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Probenazole; Oryzemate;
IUPAC/Chemical Name
3-(allyloxy)benzo[d]isothiazole 1,1-dioxide
InChi Key
WHHIPMZEDGBUCC-UHFFFAOYSA-N
InChi Code
1S/C10H9NO3S/c1-2-7-14-10-8-5-3-4-6-9(8)15(12,13)11-10/h2-6H,1,7H2
SMILES Code
C=CCOC1=NS(=O)(=O)C2=C1C=CC=C2
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 223.25 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.

Recalculate based on batch purity %
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
1: Wu Z, Wang G, Zhang B, Dai T, Gu A, Li X, Cheng X, Liu P, Hao J, Liu X. Metabolic Mechanism of Plant Defense against Rice Blast Induced by Probenazole. Metabolites. 2021 Apr 16;11(4):246. doi: 10.3390/metabo11040246. PMID: 33923492; PMCID: PMC8073365. 2: Iwai T, Seo S, Mitsuhara I, Ohashi Y. Probenazole-induced accumulation of salicylic acid confers resistance to Magnaporthe grisea in adult rice plants. Plant Cell Physiol. 2007 Jul;48(7):915-24. doi: 10.1093/pcp/pcm062. Epub 2007 May 21. PMID: 17517758. 3: Yoshioka K, Nakashita H, Klessig DF, Yamaguchi I. Probenazole induces systemic acquired resistance in Arabidopsis with a novel type of action. Plant J. 2001 Jan;25(2):149-57. doi: 10.1046/j.1365-313x.2001.00952.x. PMID: 11169191. 4: Zhang D, Zhu Z, Gao J, Zhou X, Zhu S, Wang X, Wang X, Ren G, Kuai B. The NPR1-WRKY46-WRKY6 signaling cascade mediates probenazole/salicylic acid-elicited leaf senescence in Arabidopsis thaliana. J Integr Plant Biol. 2021 May;63(5):924-936. doi: 10.1111/jipb.13044. Epub 2021 Mar 8. PMID: 33270345. 5: Yi X, Lu Y. Residues and dynamics of probenazole in rice field ecosystem. Chemosphere. 2006 Oct;65(4):639-43. doi: 10.1016/j.chemosphere.2006.01.066. Epub 2006 Mar 10. PMID: 16529792. 6: Nakashita H, Yoshioka K, Takayama M, Kuga R, Midoh N, Usami R, Horikoshi K, Yoneyama K, Yamaguchi I. Characterization of PBZ1, a probenazole-inducible gene, in suspension-cultured rice cells. Biosci Biotechnol Biochem. 2001 Jan;65(1):205-8. doi: 10.1271/bbb.65.205. PMID: 11272832. 7: Zhu Z, Gao J, Yang JX, Wang XY, Ren GD, Ding YL, Kuai BK. Synthetic promoters consisting of defined cis-acting elements link multiple signaling pathways to probenazole-inducible system. J Zhejiang Univ Sci B. 2015 Apr;16(4):253-63. doi: 10.1631/jzus.B1400203. Erratum in: J Zhejiang Univ Sci B. 2015 May;16(5):412. doi: 10.1631/jzus.B14e0203. PMID: 25845359; PMCID: PMC4399426. 8: Lin YZ, Chen HY, Kao R, Chang SP, Chang SJ, Lai EM. Proteomic analysis of rice defense response induced by probenazole. Phytochemistry. 2008 Feb;69(3):715-28. doi: 10.1016/j.phytochem.2007.09.005. Epub 2007 Oct 22. PMID: 17950386. 9: Midoh N, Iwata M. Cloning and characterization of a probenazole-inducible gene for an intracellular pathogenesis-related protein in rice. Plant Cell Physiol. 1996 Jan;37(1):9-18. doi: 10.1093/oxfordjournals.pcp.a028918. PMID: 8720923. 10: Mahmood T, Kakishima M, Komatsu S. Proteome analysis of probenazole-effect in rice-bacterial blight interactions. Protein Pept Lett. 2009;16(9):1041-52. doi: 10.2174/092986609789055331. PMID: 19799551. 11: Tanaka N, Matsuoka M, Kitano H, Asano T, Kaku H, Komatsu S. gid1, a gibberellin-insensitive dwarf mutant, shows altered regulation of probenazole- inducible protein (PBZ1) in response to cold stress and pathogen attack. Plant Cell Environ. 2006 Apr;29(4):619-31. doi: 10.1111/j.1365-3040.2005.01441.x. PMID: 17080612. 12: Kim SG, Kim ST, Wang Y, Yu S, Choi IS, Kim YC, Kim WT, Agrawal GK, Rakwal R, Kang KY. The RNase activity of rice probenazole-induced protein1 (PBZ1) plays a key role in cell death in plants. Mol Cells. 2011 Jan;31(1):25-31. doi: 10.1007/s10059-011-0004-z. Epub 2010 Nov 23. PMID: 21110127; PMCID: PMC3906867. 13: Kim ST, Kim SG, Kang YH, Wang Y, Kim JY, Yi N, Kim JK, Rakwal R, Koh HJ, Kang KY. Proteomics analysis of rice lesion mimic mutant (spl1) reveals tightly localized probenazole-induced protein (PBZ1) in cells undergoing programmed cell death. J Proteome Res. 2008 Apr;7(4):1750-60. doi: 10.1021/pr700878t. Epub 2008 Mar 14. PMID: 18338860. 14: Morino K, Kimizu M, Fujiwara M. Disulfide proteomics of rice cultured cells in response to OsRacl and probenazole-related immune signaling pathway in rice. Proteome Sci. 2017 Apr 13;15:6. doi: 10.1186/s12953-017-0115-3. PMID: 28413359; PMCID: PMC5390479. 15: Nishioka K, Takahata H, Yasuno H, Muramoto G. Occupational contact dermatitis caused by probenazole in agricultural chemical factories. Contact Dermatitis. 2009 Dec;61(6):350-1. doi: 10.1111/j.1600-0536.2009.01613.x. PMID: 20059496. 16: Zhu Z, Gao J, Yang JX, Wang XY, Ren GD, Ding YL, Kuai BK. Erratum to: Synthetic promoters consisting of defined cis-acting elements link multiple signaling pathways to probenazole-inducible system. J Zhejiang Univ Sci B. 2015 May;16(5):412. doi: 10.1631/jzus.B14e0203. Erratum for: J Zhejiang Univ Sci B. 2015 Apr;16(4):253-63. doi: 10.1631/jzus.B1400203. PMID: 25990059; PMCID: PMC4432994. 17: Zhao XH, Yang JX, Gao J, Zhou Q, Kuai BK. Analysis of probenazole- responsiveness of rice RPR1 upstream fragments. Zhi Wu Sheng Li Yu Fen Zi Sheng Wu Xue Xue Bao. 2007 Dec;33(6):524-30. PMID: 18349506. 18: Takatsuji H. Development of disease-resistant rice using regulatory components of induced disease resistance. Front Plant Sci. 2014 Nov 13;5:630. doi: 10.3389/fpls.2014.00630. PMID: 25431577; PMCID: PMC4230042. 19: Umemura K, Satou J, Iwata M, Uozumi N, Koga J, Kawano T, Koshiba T, Anzai H, Mitomi M. Contribution of salicylic acid glucosyltransferase, OsSGT1, to chemically induced disease resistance in rice plants. Plant J. 2009 Feb;57(3):463-72. doi: 10.1111/j.1365-313X.2008.03697.x. Epub 2008 Sep 26. PMID: 18826428. 20: Seth S. A Comprehensive Review on Recent advances in Synthesis & Pharmacotherapeutic potential of Benzothiazoles. Antiinflamm Antiallergy Agents Med Chem. 2015;14(2):98-112. doi: 10.2174/1871523014666150528110703. PMID: 26017385.