Pyrimorph | CAS#868390-90-3

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

MedKoo CAT#: 561001

CAS#: 868390-90-3

Description: Pyrimorph is a fungicide with high activity against the plant pathogen Phytophthora capsici. Pyrimorph inhibited different stages in the life cycle of P. capsici including mycelial growth, sporangium production, zoospore release, and cystospore germination with EC(50) values of 1.84, 0.17, 4.92, and 0.09 microg mL(-1), respectively.

Chemical Structure

Pyrimorph

CAS# 868390-90-3

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 561001
Name: Pyrimorph
CAS#: 868390-90-3
Chemical Formula: C22H25ClN2O2
Exact Mass: 384.16
Molecular Weight: 384.900
Elemental Analysis: C, 68.65; H, 6.55; Cl, 9.21; N, 7.28; O, 8.31

Price and Availability

Size	Price	Availability
50mg	USD 450	2 Weeks
100mg	USD 950	2 Weeks
200mg	USD 1650	2 Weeks
500mg	USD 2950	2 Weeks
1g	USD 4650	2 Weeks
2g	USD 6850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Pyrimorph.

IUPAC/Chemical Name: (Z)-3-(4-tert-Butylphenyl)-3-(2-chloropyridin-4-yl)-1-morpholin-4-ylprop-2-en-1-one

InChi Key: QEUOHPLVFSQWME-CYVLTUHYSA-N

InChi Code: InChI=1S/C22H25ClN2O2/c1-22(2,3)18-6-4-16(5-7-18)19(17-8-9-24-20(23)14-17)15-21(26)25-10-12-27-13-11-25/h4-9,14-15H,10-13H2,1-3H3/b19-15-

SMILES Code: O=C(N1CCOCC1)/C=C(C2=CC=C(C(C)(C)C)C=C2)\C3=CC(Cl)=NC=C3

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: >2 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:

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Biological target:	Pyrimorph is active against P. infestans, P. capsica, and R. solani (EC50s = 1.36, 0.72, and 4.44 µg/ml, respectively). Pyrimorph is toxic to zebrafish (LC50 = 19.8 mg/L).
In vitro activity:	Pyrimorph exhibited strong inhibitory effects on multiple stages of the Phytophthora capsici’s life cycle, including mycelial growth, sporangium production, zoospore release, and cystospore germination. Pyrimorph impaired the energy generation system. Additionally, pyrimorph displayed inhibitory effects on various metabolic pathways, particularly the hexose monophosphate pathway. Reference: J Agric Food Chem. 2010 Mar 10;58(5):2720-5. https://pubmed.ncbi.nlm.nih.gov/20000417/
In vivo activity:	Pyrimorph has low toxicity to zebrafish; however, it showed medium bioconcentration factor to zebrafish. The 48, 72 and 96 h median lethal concentration values of pyrimorph to zebrafish were 24.33, 22.61 and 19.79 mg L(-1) respectively. The highest bioconcentration factor of pyrimorph in the fish were 1.07 × 10(2) (144 h) and 23.1 (96 h) after exposure to 2.00 and 0.25 mg L(-1) of pyrimorph respectively. Reference: Pest Manag Sci. 2011 Sep;67(9):1178-83. https://pubmed.ncbi.nlm.nih.gov/21567892/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	1.0	2.60

Preparing Stock Solutions

The following data is based on the product molecular weight 384.90 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. Pang Z, Chen L, Miao J, Wang Z, Bulone V, Liu X. Proteomic profile of the plant-pathogenic oomycete Phytophthora capsici in response to the fungicide pyrimorph. Proteomics. 2015 Sep;15(17):2972-82. doi: 10.1002/pmic.201400502. Epub 2015 Jun 8. PMID: 25914214. 2. Yan X, Qin W, Sun L, Qi S, Yang D, Qin Z, Yuan H. Study of inhibitory effects and action mechanism of the novel fungicide pyrimorph against Phytophthora capsici. J Agric Food Chem. 2010 Mar 10;58(5):2720-5. doi: 10.1021/jf902410x. PMID: 20000417. 3. Zhao C, Liu B, Wang J, Li N, Qin Z, Qiu L. Acute toxicity and bioconcentration of pyrimorph in zebrafish, Brachydanio rerio. Pest Manag Sci. 2011 Sep;67(9):1178-83. doi: 10.1002/ps.2198. Epub 2011 May 12. PMID: 21567892.
In vitro protocol:	1. Pang Z, Chen L, Miao J, Wang Z, Bulone V, Liu X. Proteomic profile of the plant-pathogenic oomycete Phytophthora capsici in response to the fungicide pyrimorph. Proteomics. 2015 Sep;15(17):2972-82. doi: 10.1002/pmic.201400502. Epub 2015 Jun 8. PMID: 25914214. 2. Yan X, Qin W, Sun L, Qi S, Yang D, Qin Z, Yuan H. Study of inhibitory effects and action mechanism of the novel fungicide pyrimorph against Phytophthora capsici. J Agric Food Chem. 2010 Mar 10;58(5):2720-5. doi: 10.1021/jf902410x. PMID: 20000417.
In vivo protocol:	1. Zhao C, Liu B, Wang J, Li N, Qin Z, Qiu L. Acute toxicity and bioconcentration of pyrimorph in zebrafish, Brachydanio rerio. Pest Manag Sci. 2011 Sep;67(9):1178-83. doi: 10.1002/ps.2198. Epub 2011 May 12. PMID: 21567892.

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1: Pang Z, Chen L, Miao J, Wang Z, Bulone V, Liu X. Proteomic profile of the plant-pathogenic oomycete Phytophthora capsici in response to the fungicide pyrimorph. Proteomics. 2015 Sep;15(17):2972-82. doi: 10.1002/pmic.201400502. Epub 2015 Jun 8. PubMed PMID: 25914214.

2: Pang Z, Shao J, Chen L, Lu X, Hu J, Qin Z, Liu X. Resistance to the novel fungicide pyrimorph in Phytophthora capsici: risk assessment and detection of point mutations in CesA3 that confer resistance. PLoS One. 2013;8(2):e56513. doi: 10.1371/journal.pone.0056513. Epub 2013 Feb 19. PubMed PMID: 23431382; PubMed Central PMCID: PMC3576395.

3: Zhao C, Liu B, Wang J, Li N, Qin Z, Qiu L. Acute toxicity and bioconcentration of pyrimorph in zebrafish, Brachydanio rerio. Pest Manag Sci. 2011 Sep;67(9):1178-83. doi: 10.1002/ps.2198. Epub 2011 May 12. PubMed PMID: 21567892.

4: Wang J, Zhao L, Li X, Jiang Y, Li N, Qin Z, Pan C. Residue dynamic of pyrimorph on tomatoes, cucumbers and soil under greenhouse trails. Bull Environ Contam Toxicol. 2011 Mar;86(3):326-30. doi: 10.1007/s00128-011-0201-7. Epub 2011 Feb 5. PubMed PMID: 21298253.

5: Xiao YM, Esser L, Zhou F, Li C, Zhou YH, Yu CA, Qin ZH, Xia D. Studies on inhibition of respiratory cytochrome bc1 complex by the fungicide pyrimorph suggest a novel inhibitory mechanism. PLoS One. 2014 Apr 3;9(4):e93765. doi: 10.1371/journal.pone.0093765. eCollection 2014. PubMed PMID: 24699450; PubMed Central PMCID: PMC3974799.

6: Pang Z, Shao J, Hu J, Chen L, Wang Z, Qin Z, Liu X. Competition between pyrimorph-sensitive and pyrimorph-resistant isolates of Phytophthora capsici. Phytopathology. 2014 Mar;104(3):269-74. doi: 10.1094/PHYTO-07-13-0185-R. PubMed PMID: 24093920.

7: Li X, Han X, He M, Xiao Y, Qin Z. Synthesis and fungicidal activity of 1,1-diaryl tertiary alcohols. Bioorg Med Chem Lett. 2016 Dec 15;26(24):5936-5942. doi: 10.1016/j.bmcl.2016.10.090. Epub 2016 Nov 1. PubMed PMID: 27838182.

8: Yan X, Qin W, Sun L, Qi S, Yang D, Qin Z, Yuan H. Study of inhibitory effects and action mechanism of the novel fungicide pyrimorph against Phytophthora capsici. J Agric Food Chem. 2010 Mar 10;58(5):2720-5. doi: 10.1021/jf902410x. PubMed PMID: 20000417.

9: Huang JL, Xiao YM, Liu JP, Fu B, Wu YH, Ren WH, Li N, Qin ZH. [The functional mechanism between the pesticide Pyrimorph and humic acid]. Guang Pu Xue Yu Guang Pu Fen Xi. 2008 Aug;28(8):1866-9. Chinese. PubMed PMID: 18975821.

10: Wang H, Sun H, Stammler G, Ma J, Zhou M. Generation and characterization of isolates of Peronophythora litchii resistant to carboxylic acid amide fungicides. Phytopathology. 2010 May;100(5):522-7. doi: 10.1094/PHYTO-100-5-0522. PubMed PMID: 20373974.

11: Xiao Y, Yang X, Li B, Yuan H, Wan S, Xu Y, Qin Z. Design, synthesis and antifungal/insecticidal evaluation of novel cinnamide derivatives. Molecules. 2011 Oct 25;16(11):8945-57. doi: 10.3390/molecules16118945. PubMed PMID: 22027951.

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