Synonym
Carpropamid; UNII-ZS46TAN742
IUPAC/Chemical Name
Cyclopropanecarboxamide, 2,2-dichloro-N-(1-(4-chlorophenyl)ethyl)-1-ethyl-3-methyl-
InChi Key
RXDMAYSSBPYBFW-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H18Cl3NO/c1-4-14(10(3)15(14,17)18)13(20)19-9(2)11-5-7-12(16)8-6-11/h5-10H,4H2,1-3H3,(H,19,20)
SMILES Code
O=C(C1(CC)C(Cl)(Cl)C1C)NC(C2=CC=C(Cl)C=C2)C
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
334.67
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 |
1: Takagaki M, Kaku K, Watanabe S, Kawai K, Shimizu T, Sawada H, Kumakura K, Nagayama K. Mechanism of resistance to carpropamid in Magnaporthe grisea. Pest Manag Sci. 2004 Sep;60(9):921-6. doi: 10.1002/ps.896. PMID: 15382507.
2: Nakasako M, Motoyama T, Kurahashi Y, Yamaguchi I. Cryogenic X-ray crystal structure analysis for the complex of scytalone dehydratase of a rice blast fungus and its tight-binding inhibitor, carpropamid: the structural basis of tight-binding inhibition. Biochemistry. 1998 Jul 14;37(28):9931-9. doi: 10.1021/bi980321b. PMID: 9665698.
3: Rohilla R, Singh US, Singh RL. Uptake and translocation of carpropamid in rice (Oryza sativa L). Pest Manag Sci. 2001 Mar;57(3):239-47. doi: 10.1002/ps.255. PMID: 11455653.
4: Yamada N, Motoyama T, Nakasako M, Kagabu S, Kudo T, Yamaguchi I. Enzymatic characterization of scytalone dehydratase Val75Met variant found in melanin biosynthesis dehydratase inhibitor (MBI-D) resistant strains of the rice blast fungus. Biosci Biotechnol Biochem. 2004 Mar;68(3):615-21. doi: 10.1271/bbb.68.615. PMID: 15056895.
5: Lim W, Konings M, Parel F, Eadie K, Strepis N, Fahal A, Verbon A, van de Sande WWJ. Inhibiting DHN- and DOPA-melanin biosynthesis pathway increased the therapeutic value of itraconazole in Madurella mycetomatis infected Galleria mellonella. Med Mycol. 2022 Feb 2;60(2):myac003. doi: 10.1093/mmy/myac003. PMID: 35064672; PMCID: PMC9295015.
6: Yasukochi H, Atago T, Tanaka A, Nakatsuji H, Yoshida E, Kakehi A, Nishii Y, Tanabe Y. Practical, general, and systematic method for optical resolution of gem-dihalo- and monohalocyclopropanecarboxylic acids utilizing chiral 1,1'-binaphtholmonomethyl ethers: application to the synthesis of three chiral pesticides. Org Biomol Chem. 2008 Feb 7;6(3):540-7. doi: 10.1039/b714614k. Epub 2007 Dec 18. PMID: 18219425.
7: Yu Q, Cao ZY, Dong JG. [Cloning and functional analysis of scytalone dehytratase gene in Exserohilum turcicum]. Wei Sheng Wu Xue Bao. 2007 Dec;47(6):1013-8. Chinese. PMID: 18271256.
8: Sawada H, Sugihara M, Takagaki M, Nagayama K. Monitoring and characterization of Magnaporthe grisea isolates with decreased sensitivity to scytalone dehydratase inhibitors. Pest Manag Sci. 2004 Aug;60(8):777-85. doi: 10.1002/ps.858. PMID: 15307669.
9: Kaku K, Takagaki M, Shimizu T, Nagayama K. Diagnosis of dehydratase inhibitors in melanin biosynthesis inhibitor (MBI-D) resistance by primer- introduced restriction enzyme analysis in scytalone dehydratase gene of Magnaporthe grisea. Pest Manag Sci. 2003 Aug;59(8):843-6. doi: 10.1002/ps.742. PMID: 12916764.
