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MedKoo Cat#: 461651 | Name: Procymidone
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Description:

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

Procymidone is a dicarboximide fungicide mainly used for vineyard protection but also for different crops.

Chemical Structure

Procymidone
CAS#32809-16-8

Theoretical Analysis

MedKoo Cat#: 461651

Name: Procymidone

CAS#: 32809-16-8

Chemical Formula: C13H11Cl2NO2

Exact Mass: 283.0167

Molecular Weight: 284.14

Elemental Analysis: C, 54.95; H, 3.90; Cl, 24.95; N, 4.93; O, 11.26

Price and Availability

Size Price Availability Quantity
250mg USD 375.00
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Synonym
Procymidone; Dicyclidine; S 7131; S-7131; S7131; SP 751011; SP-751011; SP751011; Sumilex; Sumisclex;
IUPAC/Chemical Name
3-(3,5-dichlorophenyl)-1,5-dimethyl-3-azabicyclo[3.1.0]hexane-2,4-dione
InChi Key
QXJKBPAVAHBARF-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H11Cl2NO2/c1-12-6-13(12,2)11(18)16(10(12)17)9-4-7(14)3-8(15)5-9/h3-5H,6H2,1-2H3
SMILES Code
O=C(C1(C)C2(C)C1)N(C3=CC(Cl)=CC(Cl)=C3)C2=O
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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Procymidone is a dicarboximide fungicide mainly used for vineyard protection but also for different crops.
In vitro activity:
Procymidone 100 microM stimulated cell growth from day 3 up to day 12 and raised the level of pS2 on day 3. This study found that procymidone induced mitogen-activated protein kinase (MAPK) at 15 and 30 min, and that PD 98059, a MAPK (Erk1/2) inhibitor, prevented procymidone's effects on cell growth and pS2, indicating that MAPK activation is responsible for procymidone ER activation. Reference: Life Sci. 2006 May 1;78(23):2716-23. https://pubmed.ncbi.nlm.nih.gov/16310225/
In vivo activity:
Maternal PRO (procymidone) exposure affected the growth phenotypes and the glucolipid metabolism related indicators and genes of mice, especially the male mice of F1 generations. The changes in bile acids (BAs) metabolism demonstrated that PRO disordered glucolipid metabolism through enterohepatic circulation. Furthermore, PRO reduced mucus secretion in the gut and altered the composition of gut microbiota, leading more bacteria to disseminate in the gut and inflammatory responses both in F0 and F1 regenerations. And PRO-induced gut microbiota dysbiosis was tightly related to BAs metabolites. Reference: Food Chem Toxicol. 2023 Apr;174:113657. https://pubmed.ncbi.nlm.nih.gov/36764477/

Preparing Stock Solutions

The following data is based on the product molecular weight 284.14 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
Formulation protocol:
1. Radice S, Chiesara E, Frigerio S, Fumagalli R, Parolaro D, Rubino T, Marabini L. Estrogenic effect of procymidone through activation of MAPK in MCF-7 breast carcinoma cell line. Life Sci. 2006 May 1;78(23):2716-23. doi: 10.1016/j.lfs.2005.10.008. Epub 2005 Nov 28. PMID: 16310225. 2. Wang X, Weng Y, Geng S, Wang C, Jin C, Shi L, Jin Y. Maternal procymidone exposure has lasting effects on murine gut-liver axis and glucolipid metabolism in offspring. Food Chem Toxicol. 2023 Apr;174:113657. doi: 10.1016/j.fct.2023.113657. Epub 2023 Feb 9. PMID: 36764477. 3. Wang Z, Li R, Yan Z, Fu H, Zhu Y. [Injury of procymidone on testis and sperm in the male adolescent mice]. Wei Sheng Yan Jiu. 2020 Nov;49(6):949-954. Chinese. doi: 10.19813/j.cnki.weishengyanjiu.2020.06.013. PMID: 33413771.
In vitro protocol:
1. Radice S, Chiesara E, Frigerio S, Fumagalli R, Parolaro D, Rubino T, Marabini L. Estrogenic effect of procymidone through activation of MAPK in MCF-7 breast carcinoma cell line. Life Sci. 2006 May 1;78(23):2716-23. doi: 10.1016/j.lfs.2005.10.008. Epub 2005 Nov 28. PMID: 16310225.
In vivo protocol:
1. Wang X, Weng Y, Geng S, Wang C, Jin C, Shi L, Jin Y. Maternal procymidone exposure has lasting effects on murine gut-liver axis and glucolipid metabolism in offspring. Food Chem Toxicol. 2023 Apr;174:113657. doi: 10.1016/j.fct.2023.113657. Epub 2023 Feb 9. PMID: 36764477. 2. Wang Z, Li R, Yan Z, Fu H, Zhu Y. [Injury of procymidone on testis and sperm in the male adolescent mice]. Wei Sheng Yan Jiu. 2020 Nov;49(6):949-954. Chinese. doi: 10.19813/j.cnki.weishengyanjiu.2020.06.013. PMID: 33413771.
1: Lu J, Guo Y, Shan X, Song Y, Li R, Tian L, Li X. Solid electrochemiluminescence sensor by immobilization luminol in Zn-Co-ZIF CNFs for sensitive detection of procymidone in vegetables. Mikrochim Acta. 2024 Aug 5;191(9):508. doi: 10.1007/s00604-024-06582-z. PMID: 39102114. 2: Thomaes A, Bervoets L, Storms L. Preliminary Evaluation of Historical used Pesticides in Quercus robur Wood in Belgium: a Negative Finding. Bull Environ Contam Toxicol. 2024 Jul 27;113(2):18. doi: 10.1007/s00128-024-03932-8. PMID: 39068286. 3: Dong H, Wang H, Guo Z, Huang J, Zhang P, Guo Y, Sun X. Combination of Capture-SELEX and Post-SELEX for procymidone-specific aptamer selection and broad-specificity aptamer discovery, and development of aptamer-based lateral flow assay. Anal Chim Acta. 2024 Aug 22;1318:342922. doi: 10.1016/j.aca.2024.342922. Epub 2024 Jun 29. PMID: 39067914. 4: Khoury D, Jabali Y, Delhomme O, Millet M. Pesticide occurrence and distribution in fogwater collected at four sites at Strasbourg metropolitan between 2015 and 2021. Environ Pollut. 2024 Jul 15;359:124564. doi: 10.1016/j.envpol.2024.124564. Epub ahead of print. PMID: 39019311. 5: Yun HY, Kim IS, Shin KH. Compound-Specific Isotope Analysis Provides Direct Evidence for Identifying the Source of Residual Pesticides Diazinon and Procymidone in the Soil-Plant System. J Agric Food Chem. 2024 May 29;72(21):11980-11989. doi: 10.1021/acs.jafc.4c00640. Epub 2024 May 17. PMID: 38758169. 6: Wang R, He B, Wang Y, Liu Y, Liang Z, Jin H, Wei M, Ren W, Suo Z, Xu Y. A novel electrochemical aptasensor based on AgPdNPs/PEI-GO and hollow nanobox-like Pt@Ni-CoHNBs for procymidone detection. Bioelectrochemistry. 2024 Aug;158:108728. doi: 10.1016/j.bioelechem.2024.108728. Epub 2024 May 8. PMID: 38733721. 7: Wei L, Chen B, Li J, Zhang P, Chen W, Ye W, Chen C. Resistance mechanism of Phomopsis longicolla to fludioxonil is associated with modifications in PlOS1, PlOS4 and PlOS5. Pestic Biochem Physiol. 2024 May;201:105862. doi: 10.1016/j.pestbp.2024.105862. Epub 2024 Mar 16. PMID: 38685239. 8: Wu Z, Yu C, Bi Q, Zhang J, Hao J, Liu P, Liu X. Procymidone Application Contributes to Multidrug Resistance of Botrytis cinerea. J Fungi (Basel). 2024 Mar 29;10(4):261. doi: 10.3390/jof10040261. PMID: 38667931; PMCID: PMC11050779. 9: Wang R, He B, Yang J, Liu Y, Liang Z, Jin H, Wei M, Ren W, Suo Z, Xu Y. A fluorescence-electrochemical dual-mode aptasensor based on novel DNA-dependent PBNFs@PtPd for highly selective and sensitive detection of procymidone through hybridization chain reaction. Sci Total Environ. 2024 Jun 10;928:172529. doi: 10.1016/j.scitotenv.2024.172529. Epub 2024 Apr 15. PMID: 38631626. 10: Li F, Wang X, Zhang J, Nie H, He S, Li Y, Xia R, Zhu Y. Low levels of Cd2+ combined with procymidone may cause ovarian damage in mice via unfolded protein response. Environ Toxicol. 2024 May;39(5):3160-3171. doi: 10.1002/tox.24169. Epub 2024 Feb 7. PMID: 38323353. 11: Wei L, Chen B, Li X, Shi H, Xie S, Hu H, Chen W, Wei L, Wang X, Chen C. The HOG-pathway related AaOS1 leads to dicarboximide-resistance in field strains of Alternaria alternata and contributes, together with the Aafhk1, to mycotoxin production and virulence. Pest Manag Sci. 2024 Jun;80(6):2937-2949. doi: 10.1002/ps.8002. Epub 2024 Feb 28. PMID: 38297826. 12: Wu S, Di S, Lv L, Wang D, Wang X, Wang Y. Enzymatic and transcriptional level changes induced by the co-presence of lead and procymidone in hook snout carp (Opsariichthys bidens). Sci Total Environ. 2024 Mar 15;916:170409. doi: 10.1016/j.scitotenv.2024.170409. Epub 2024 Jan 26. PMID: 38280588. 13: Ren W, Han W, Huan T, Zhu M, Zhang Y, Li B, Liu N. A new point mutation (D1158N) in histidine kinase Bos1 confers high-level resistance to fludioxonil in field gray mold disease. Pestic Biochem Physiol. 2024 Jan;198:105750. doi: 10.1016/j.pestbp.2023.105750. Epub 2023 Dec 16. PMID: 38225093. 14: Xin B, Wang Q, Wang X, Li F, Bai M, Fu H, Yan Z, Zhu Y, Huang X. Reduction of excessive unfolded protein response by 4-phenylbutyric acid may mitigate procymidone-induced testicular damage in mice by changing the levels of circRNA Scar and circZc3h4. Pestic Biochem Physiol. 2023 Dec;197:105689. doi: 10.1016/j.pestbp.2023.105689. Epub 2023 Nov 9. PMID: 38072544. 15: Deng Y, Wang T, Du Y, Zhang L, Wang J, Qi Z, Ji M. Risk assessment for resistance to fludioxonil in Corynespora cassiicola in Liaoning China. Pestic Biochem Physiol. 2023 Dec;197:105622. doi: 10.1016/j.pestbp.2023.105622. Epub 2023 Sep 16. PMID: 38072516. 16: Li G, Zhang L, Wang H, Li X, Cheng F, Miao J, Peng Q, Liu X. Resistance to the DMI fungicide mefentrifluconazole in Monilinia fructicola: risk assessment and resistance basis analysis. Pest Manag Sci. 2024 Apr;80(4):1802-1811. doi: 10.1002/ps.7909. Epub 2023 Dec 21. PMID: 38029343. 17: Li R, Li F, Wang X, Bai M, Fu H, Yan Z, Yang X, Zhu Y. 4-Phenylbutyric acid may prevent mouse ovarian and uterine damage due to procymidone-induced alteration of circRNA Scar and circZc3h4 levels by controlling excessive unfolded protein response. Pestic Biochem Physiol. 2023 Nov;196:105631. doi: 10.1016/j.pestbp.2023.105631. Epub 2023 Sep 28. PMID: 37945263. 18: Suo K, Zhang Y, Feng Y, Yang Z, Zhou C, Chen W, Wang J. Ultrasonic synergistic slightly acidic electrolyzed water processing to improve postharvest storage quality of Chinese bayberry. Ultrason Sonochem. 2023 Dec;101:106668. doi: 10.1016/j.ultsonch.2023.106668. Epub 2023 Oct 30. PMID: 37918295; PMCID: PMC10638035. 19: Sun P, Ding G, Ren D, Han Y, Gao T, Fang Y, Ma H, Li W. Pesticide residues in agricultural end-products and risk assessment for consumers in North China. Environ Monit Assess. 2023 Oct 31;195(11):1392. doi: 10.1007/s10661-023-12005-y. PMID: 37906343. 20: Jiang H, Zhao M, Chen Q. Determination of procymidone residues in rapeseed oil based on olfactory visualization technology. Food Chem X. 2023 Jul 17;19:100794. doi: 10.1016/j.fochx.2023.100794. PMID: 37780316; PMCID: PMC10534118.