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MedKoo Cat#: 461039 | Name: Pirimiphos-methyl
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Description:

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

Pirimiphos-methyl (PMM) is a widely used organophosphorus pesticide that can be released into the atmosphere in gas and condensed phases.

Chemical Structure

Pirimiphos-methyl
Pirimiphos-methyl
CAS#29232-93-7

Theoretical Analysis

MedKoo Cat#: 461039

Name: Pirimiphos-methyl

CAS#: 29232-93-7

Chemical Formula: C11H20N3O3PS

Exact Mass: 305.0963

Molecular Weight: 305.33

Elemental Analysis: C, 43.27; H, 6.60; N, 13.76; O, 15.72; P, 10.14; S, 10.50

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
250mg USD 600.00 2 weeks
500mg USD 900.00 2 Weeks
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Related CAS #
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Synonym
Pirimiphos-methyl; Actelic; AI3-27699; Caswell No. 334B; PP511; R 33986; R-33986; R33986;
IUPAC/Chemical Name
O-(2-(diethylamino)-6-methylpyrimidin-4-yl) O,O-dimethyl phosphorothioate
InChi Key
QHOQHJPRIBSPCY-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H20N3O3PS/c1-6-14(7-2)11-12-9(3)8-10(13-11)17-18(19,15-4)16-5/h8H,6-7H2,1-5H3
SMILES Code
S=P(OC)(OC1=NC(N(CC)CC)=NC(C)=C1)OC
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:
Pirimiphos-methyl is a rapid-acting organophosphorus insecticide and acaricide, causing inhibition of AChE in target organisms.
In vitro activity:
Pirimiphos-methyl is an organophosphate (OP) insecticide, causing inhibition of acetylcholinesterase in target organisms. The aim of this study was to examine pirimiphos-methyl non-targeted mode of action toxicity in Atlantic salmon using in vitro exposure. Hepatocyte cells were exposed to pirimiphos-methyl (control-0.1-1.0-10-100-1000μM) for 48h. The results showed that the compound acts cytotoxic and impacts accumulation of lipids (steatosis) at 1000μM. Metabolomics screening revealed effects on lipid metabolism (diHOME fatty acids, cholesterol and lysophospholipids), glutathione (depletion), glycolysis and tryptophan metabolism, as well as on several vitamins. At 1000μM, vitamin E levels increased, while folate and thiamine derivate levels decreased. Surprisingly few transcripts were affected by the treatment, with only 64 differentially expressed genes (DEGs) showing a clear dose-dependent response. Reference: Toxicol In Vitro. 2017 Mar;39:1-14. https://pubmed.ncbi.nlm.nih.gov/27845199/
In vivo activity:
This study was carried out to assess the immunologic effects of POM (pirimiphos-methyl) in Balb/c mice after 28-day oral exposure. Three dose levels of POM (10, 60, or 120 mg/kg/day) were administered orally to mice for 4 weeks. At autopsy after 28-day exposure, there were significant decreases in relative spleen weight and splenic cellularity found at 120 mg POM, but body weight, relative thymic weight, thymic cellularity, and splenic and thymic subsets were not affected. Oral exposure to POM induced a significant decrease in Immunoglobulin M production capability in Balb/c mice. This decrease in antibody production capability may result from disturbances in cytokine balance produced by splenic immune cells. These results show that POM may induce allergic responses by relatively enhancing T(H)2 development and additionally contribute to chronic inflammation by attracting macrophage by IFN-gamma. Reference: J Toxicol Environ Health A. 2007 Aug;70(15-16):1278-87. https://pubmed.ncbi.nlm.nih.gov/17654245/
Solvent mg/mL mM comments
Solubility
DMSO 50.0 163.76
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 305.33 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. Olsvik PA, Berntssen MHG, Søfteland L. In vitro toxicity of pirimiphos-methyl in Atlantic salmon hepatocytes. Toxicol In Vitro. 2017 Mar;39:1-14. doi: 10.1016/j.tiv.2016.11.008. Epub 2016 Nov 12. PMID: 27845199. 2. Borrás E, Ródenas M, Vera T, Gómez T, Muñoz A. Atmospheric degradation of the organothiophosphate insecticide - Pirimiphos-methyl. Sci Total Environ. 2017 Feb 1;579:1-9. doi: 10.1016/j.scitotenv.2016.11.009. Epub 2016 Nov 21. PMID: 27881242. 3. Kim HS, Eom JH, Cho HY, Cho YJ, Kim JY, Lee JK, Kim SH, Park KL. Evaluation of immunotoxicity induced by pirimiphos-methyl in male Balb/c mice following exposure to for 28 days. J Toxicol Environ Health A. 2007 Aug;70(15-16):1278-87. doi: 10.1080/15287390701434372. PMID: 17654245. 4. Ngoula F, Watcho P, Dongmo MC, Kenfack A, Kamtchouing P, Tchoumboué J. Effects of pirimiphos-methyl (an organophosphate insecticide) on the fertility of adult male rats. Afr Health Sci. 2007 Mar;7(1):3-9. doi: 10.5555/afhs.2007.7.1.3. PMID: 17604518; PMCID: PMC2366127.
In vitro protocol:
1. Olsvik PA, Berntssen MHG, Søfteland L. In vitro toxicity of pirimiphos-methyl in Atlantic salmon hepatocytes. Toxicol In Vitro. 2017 Mar;39:1-14. doi: 10.1016/j.tiv.2016.11.008. Epub 2016 Nov 12. PMID: 27845199. 2. Borrás E, Ródenas M, Vera T, Gómez T, Muñoz A. Atmospheric degradation of the organothiophosphate insecticide - Pirimiphos-methyl. Sci Total Environ. 2017 Feb 1;579:1-9. doi: 10.1016/j.scitotenv.2016.11.009. Epub 2016 Nov 21. PMID: 27881242.
In vivo protocol:
1. Kim HS, Eom JH, Cho HY, Cho YJ, Kim JY, Lee JK, Kim SH, Park KL. Evaluation of immunotoxicity induced by pirimiphos-methyl in male Balb/c mice following exposure to for 28 days. J Toxicol Environ Health A. 2007 Aug;70(15-16):1278-87. doi: 10.1080/15287390701434372. PMID: 17654245. 2. Ngoula F, Watcho P, Dongmo MC, Kenfack A, Kamtchouing P, Tchoumboué J. Effects of pirimiphos-methyl (an organophosphate insecticide) on the fertility of adult male rats. Afr Health Sci. 2007 Mar;7(1):3-9. doi: 10.5555/afhs.2007.7.1.3. PMID: 17604518; PMCID: PMC2366127.
1: Yu C, Li Y, Zhang Q, Zou N, Gu K, Li X, Pan C. Decrease of pirimiphos-methyl and deltamethrin residues in stored rice with post-harvest treatment. Int J Environ Res Public Health. 2014 May 16;11(5):5372-81. doi: 10.3390/ijerph110505372. PubMed PMID: 24840352; PubMed Central PMCID: PMC4053915. 2: Tchicaya ES, Nsanzabana C, Smith TA, Donzé J, de Hipsl ML, Tano Y, Müller P, Briët OJ, Utzinger J, Koudou BG. Micro-encapsulated pirimiphos-methyl shows high insecticidal efficacy and long residual activity against pyrethroid-resistant malaria vectors in central Côte d'Ivoire. Malar J. 2014 Aug 25;13:332. doi: 10.1186/1475-2875-13-332. PubMed PMID: 25152326; PubMed Central PMCID: PMC4159530. 3: Lee RM, Choong CT, Goh BP, Ng LC, Lam-Phua SG. Bioassay and biochemical studies of the status of pirimiphos-methyl and cypermethrin resistance in Aedes (Stegomyia) aegypti and Aedes (Stegomyia) albopictus (Diptera: Culicidae) in Singapore. Trop Biomed. 2014 Dec;31(4):670-9. PubMed PMID: 25776592. 4: Haji KA, Thawer NG, Khatib BO, Mcha JH, Rashid A, Ali AS, Jones C, Bagi J, Magesa SM, Ramsan MM, Garimo I, Greer G, Reithinger R, Ngondi JM. Efficacy, persistence and vector susceptibility to pirimiphos-methyl (Actellic 300CS) insecticide for indoor residual spraying in Zanzibar. Parasit Vectors. 2015 Dec 9;8:628. doi: 10.1186/s13071-015-1239-x. PubMed PMID: 26652708; PubMed Central PMCID: PMC4674920. 5: Oxborough RM, Kitau J, Jones R, Feston E, Matowo J, Mosha FW, Rowland MW. Long-lasting control of Anopheles arabiensis by a single spray application of micro-encapsulated pirimiphos-methyl (Actellic® 300 CS). Malar J. 2014 Jan 29;13:37. doi: 10.1186/1475-2875-13-37. PubMed PMID: 24476070; PubMed Central PMCID: PMC3914366. 6: Agossa FR, Aïkpon R, Azondékon R, Govoetchan R, Padonnou GG, Oussou O, Oké-Agbo F, Akogbéto MC. Efficacy of various insecticides recommended for indoor residual spraying: pirimiphos methyl, potential alternative to bendiocarb for pyrethroid resistance management in Benin, West Africa. Trans R Soc Trop Med Hyg. 2014 Feb;108(2):84-91. doi: 10.1093/trstmh/trt117. PubMed PMID: 24463582. 7: Anogwih JA. Toxicity of pirimiphos methyl (Actellic 25EC) on Anopheles gambiae s.s., Culex quinquefasciatus (Diptera: Culicidae), and potential biocontrol agent, Poecilia reticulata (Pisces: Poeciliidae). J Econ Entomol. 2014 Aug;107(4):1440-6. PubMed PMID: 25195433. 8: Dorđević TM, Siler-Marinković SS, Durović-Pejčev RD, Dimitrijević-Branković SI, Gajić Umiljendić JS. Dissipation of pirimiphos-methyl during wheat fermentation by Lactobacillus plantarum. Lett Appl Microbiol. 2013 Nov;57(5):412-9. doi: 10.1111/lam.12128. Epub 2013 Jul 23. PubMed PMID: 23879636. 9: Yang B, Wang Y, Shu J, Zhang P, Sun W, Li N, Zhang Y. Theoretical study on the atmospheric transformation mechanism of pirimiphos-methyl initiated by O3. Chemosphere. 2015 Nov;138:966-72. doi: 10.1016/j.chemosphere.2014.12.039. Epub 2015 Jan 3. PubMed PMID: 25563160. 10: Savi GD, Piacentini KC, Bortolotto T, Scussel VM. Degradation of bifenthrin and pirimiphos-methyl residues in stored wheat grains (Triticum aestivum L.) by ozonation. Food Chem. 2016 Jul 15;203:246-251. doi: 10.1016/j.foodchem.2016.02.069. Epub 2016 Feb 10. PubMed PMID: 26948611. 11: Stepić S, Hackenberger BK, Velki M, Lončarić Z, Hackenberger DK. Effects of individual and binary-combined commercial insecticides endosulfan, temephos, malathion and pirimiphos-methyl on biomarker responses in earthworm Eisenia andrei. Environ Toxicol Pharmacol. 2013 Sep;36(2):715-23. doi: 10.1016/j.etap.2013.06.011. Epub 2013 Jul 1. PubMed PMID: 23896224. 12: El-Moghazy AY, Soliman EA, Ibrahim HZ, Marty JL, Istamboulie G, Noguer T. Biosensor based on electrospun blended chitosan-poly (vinyl alcohol) nanofibrous enzymatically sensitized membranes for pirimiphos-methyl detection in olive oil. Talanta. 2016 Aug 1;155:258-64. doi: 10.1016/j.talanta.2016.04.018. Epub 2016 Apr 22. PubMed PMID: 27216682. 13: Rowland M, Boko P, Odjo A, Asidi A, Akogbeto M, N'Guessan R. A new long-lasting indoor residual formulation of the organophosphate insecticide pirimiphos methyl for prolonged control of pyrethroid-resistant mosquitoes: an experimental hut trial in Benin. PLoS One. 2013 Jul 23;8(7):e69516. doi: 10.1371/journal.pone.0069516. Print 2013. PubMed PMID: 23936033; PubMed Central PMCID: PMC3720653. 14: Chanda E, Chanda J, Kandyata A, Phiri FN, Muzia L, Haque U, Baboo KS. Efficacy of ACTELLIC 300 CS, pirimiphos methyl, for indoor residual spraying in areas of high vector resistance to pyrethroids and carbamates in Zambia. J Med Entomol. 2013 Nov;50(6):1275-81. PubMed PMID: 24843932. 15: Velki M, Hackenberger BK. Biomarker responses in earthworm Eisenia andrei exposed to pirimiphos-methyl and deltamethrin using different toxicity tests. Chemosphere. 2013 Jan;90(3):1216-26. doi: 10.1016/j.chemosphere.2012.09.051. Epub 2012 Oct 11. PubMed PMID: 23063481. 16: Wang Y, Yang B, Zhang P, Zhang W, Liu C, Shu X, Shu J. Heterogeneous reactions of pirimiphos-methyl and pirimicarb with NO3 radicals. J Phys Chem A. 2012 Nov 8;116(44):10802-9. doi: 10.1021/jp3071635. Epub 2012 Oct 29. PubMed PMID: 23083006. 17: Hamainza B, Sikaala CH, Moonga HB, Chanda J, Chinula D, Mwenda M, Kamuliwo M, Bennett A, Seyoum A, Killeen GF. Incremental impact upon malaria transmission of supplementing pyrethroid-impregnated long-lasting insecticidal nets with indoor residual spraying using pyrethroids or the organophosphate, pirimiphos methyl. Malar J. 2016 Feb 18;15:100. doi: 10.1186/s12936-016-1143-7. PubMed PMID: 26893012; PubMed Central PMCID: PMC4758014. 18: Lucini L, Molinari GP. Residues of pirimiphos-methyl in cereals and processed fractions following post harvest spray application. J Environ Sci Health B. 2011;46(6):518-24. doi: 10.1080/03601234.2011.583872. PubMed PMID: 21726150. 19: Fuseini G, Ebsworth P, Jones S, Knight D. The efficacy of ACTELLIC 50 EC, pirimiphos methyl, for indoor residual spraying in Ahafo, Ghana: area of high vector resistance to pyrethroids and organochlorines. J Med Entomol. 2011 Mar;48(2):437-40. PubMed PMID: 21485386. 20: Ngoula F, Watcho P, Dongmo MC, Kenfack A, Kamtchouing P, Tchoumboué J. Effects of pirimiphos-methyl (an organophosphate insecticide) on the fertility of adult male rats. Afr Health Sci. 2007 Mar;7(1):3-9. PubMed PMID: 17604518; PubMed Central PMCID: PMC2366127.

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