Synonym
Crufomate; Crufomatum; M-1261; M 1261; M1261; Ruelene; Amidofos; Amidophos; NSC 253463; NSC253463; NSC-253463;
IUPAC/Chemical Name
4-(tert-butyl)-2-chlorophenyl methyl methylphosphoramidate
InChi Key
BOFHKBLZOYVHSI-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H19ClNO3P/c1-12(2,3)9-6-7-11(10(13)8-9)17-18(15,14-4)16-5/h6-8H,1-5H3,(H,14,15)
SMILES Code
O=P(OC)(NC)OC1=CC=C(C(C)(C)C)C=C1Cl
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
291.71
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: O'Keeffe M, Eades JF, Strickland KL, Harrington D. Crufomate residues in milk and milk products following treatment of dairy cows for warble-fly. J Sci Food Agric. 1982 Apr;33(4):355-60. PubMed PMID: 6211572.
2: Bakke JE, Price CE. Metabolism of crufomate (4-tert-butyl-2-chlorophenyl methyl methylphosphoramidate) administered topically to a sheep. J Environ Sci Health B. 1979;14(4):417-26. PubMed PMID: 157364.
3: Khan MA. The toxicity of crufomate to calves exposed to warble flies (Hypoderma spp). Res Vet Sci. 1973 Sep;15(2):180-5. PubMed PMID: 4803572.
4: Feil VJ, Bakke JE, Zaylskie RG. Synthesis and mass spectrometry of crufomate metabolites and related compounds. Biomed Mass Spectrom. 1976 Dec;3(6):316-28. PubMed PMID: 137004.
5: Pekas JC, Bakke JE, Giles JL, Price CE. Rat intestinal metabolism of crufomate (4-tert-butyl-2-chlorophenyl methyl methylphosphoramidate). J Environ Sci Health B. 1977;12(4):261-8. PubMed PMID: 144749.
6: Khan MA. Reproduction in mice treated with crufomate: effects of dermal treatments on female mice and on their progeny. J Environ Sci Health B. 1978;13(3):169-81. PubMed PMID: 150439.
7: DeVaney JA, Ivie GW. Systemic activity of coumaphos, famphur, crufomate, ronnel, and phosmet given orally to hens for control of the northern fowl mite, Ornitbonyssus sulviarum (Canestrini and Fanzago). Poult Sci. 1980 Jun;59(6):1208-10. PubMed PMID: 6157151.
8: Ellington JJ, Evans JJ, Prickett KB, Champion WL Jr. High-performance liquid chromatographic separation of the enantiomers of organophosphorus pesticides on polysaccharide chiral stationary phases. J Chromatogr A. 2001 Sep 14;928(2):145-54. PubMed PMID: 11587332.
9: Khan MA. Reproduction and growth of progeny of female mice mated after treatment with crufomate. J Environ Sci Health B. 1981;16(2):141-57. PubMed PMID: 6454716.
10: Poole JB, Dooley KL. Anthelmintic efficacy of topically applied crufomate against gastrointestinal parasites in cattle. Am J Vet Res. 1972 May;33(5):1063-6. PubMed PMID: 5023045.
11: Bakke JE, Price CE. Metabolism of crufomate [(4-tert-butyl-2-chlorophenyl methyl methylphosphormidate)] by the rat. J Environ Sci Health B. 1977;12(4):251-60. PubMed PMID: 144748.
12: Bakke JE, Feil VJ, Price CE, Zaylskie RG. Metabolism of [4C]crufomate (4-t-butyl-2-chlorophenyl methyl methylphosphoramidate) by the sheep. Biomed Mass Spectrom. 1976 Dec;3(6):299-315. PubMed PMID: 137003.
13: Greenhalgh R, Dokladalova J, Haufe WO. GLC determination of crufomate (Ruelene) in bovine blood and the use of UV irradiation as a conformatory test. Bull Environ Contam Toxicol. 1972 Apr;7(4):237-42. PubMed PMID: 4669489.
14: Lyons ET, Tolliver SC, Drudge JH. Controlled test of the efficacy of the feed premix formulation of crufomate on the parasites of the gastrointestinal tract and lungs of dairy calves. Am J Vet Res. 1982 Jun;43(6):1072-4. PubMed PMID: 6213184.
15: Bakke JE, Price CE, Zaylskie RG. Mass spectral characterization of the glucuronide conjugates of crufomate (4-t-butyl-2-chlorophenyl methyl methylphosphoramidate) metabolites. Biomed Mass Spectrom. 1976 Dec;3(6):329-34. PubMed PMID: 137005.
16: Khan MA. Toxicity of systemic insecticides: efficacy of dermal and parenteral applications of crufomate for systemic control of Hypoderma spp. in cattle. Vet Rec. 1973 Nov 17;93(20):528-32. PubMed PMID: 4786116.
17: Bellows RA, Rumsey TS, Kasson CW, Bond J, Warwick EJ, Pahnish OF. Effects of organic phosphate systemic insecticides on bovine embryonic survival and development. Am J Vet Res. 1975 Aug;36(08):1133-40. PubMed PMID: 1155833.
18: Armstrong DW, Reid GL 3rd, Hilton ML, Chang CD. Relevance of enantiomeric separations in environmental science. Environ Pollut. 1993;79(1):51-8. PubMed PMID: 15091913.
19: de Jong LP, Wolring GZ, Benschop HP. Reactivation of acetylcholinesterase inhibited by methamidophos and analogous (di)methylphosphoramidates. Arch Toxicol. 1982 Jan;49(2):175-83. PubMed PMID: 7059283.
20: Lämmler G, Grüner D. Chemotherapeutic studies on Litomosoides carinii infection of Mastomys natalensis. 6. The filaricidal activity of organophosphorus compounds. Tropenmed Parasitol. 1975 Sep;26(3):359-69. PubMed PMID: 1189030.
