Pyrimorph | CAS#868390-90-3 | fungicide

MedKoo Cat#: 561001 | Name: Pyrimorph

Description:

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

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

Theoretical Analysis

MedKoo Cat#: 561001

Name: Pyrimorph

CAS#: 868390-90-3

Chemical Formula: C22H25ClN2O2

Exact Mass: 384.1605

Molecular Weight: 384.90

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 450.00	2 Weeks
100mg	USD 950.00	2 Weeks
200mg	USD 1,650.00	2 Weeks
500mg	USD 2,950.00	2 Weeks
1g	USD 4,650.00	2 Weeks
2g	USD 6,850.00	2 Weeks

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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

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	1.0	2.60

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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:

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.

1: Yin F, Liu X, Xu Y, Fu B, Zhang X, Xiao Y, Li J, Qin Z. Triphenylphosphonium- Driven Targeting of Pyrimorph Fragment Derivatives Greatly Improved Its Action on Phytopathogen Mitochondria. J Agric Food Chem. 2023 Feb 15;71(6):2842-2852. doi: 10.1021/acs.jafc.2c07902. Epub 2023 Feb 1. PMID: 36722627. 2: Nawaz K, Shahid AA, Bengyella L, Subhani MN, Ali M, Anwar W, Iftikhar S, Ali SW. Evidence of genetically diverse virulent mating types of Phytophthora capsici from Capsicum annum L. World J Microbiol Biotechnol. 2018 Aug 12;34(9):130. doi: 10.1007/s11274-018-2511-y. PMID: 30101403. 3: 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. PMID: 27838182. 4: 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. 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. PMID: 24699450; 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. PMID: 24093920. 7: 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. PMID: 23431382; PMCID: PMC3576395. 8: 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. PMID: 22027951; PMCID: PMC6264240. 9: 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. 10: 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. PMID: 21298253. 11: 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. PMID: 20373974. 12: 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. 13: 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. PMID: 18975821.