Crufomate | CAS#299-86-5 | Insecticide

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

MedKoo CAT#: 461558

CAS#: 299-86-5

Description: Crufomate is an insecticide used extensively for the control of cattle grubs, cattle lice, and hornflies.

Chemical Structure

Crufomate

CAS# 299-86-5

Instruction

Theoretical Analysis

MedKoo Cat#: 461558
Name: Crufomate
CAS#: 299-86-5
Chemical Formula: C12H19ClNO3P
Exact Mass: 291.08
Molecular Weight: 291.710
Elemental Analysis: C, 49.41; H, 6.57; Cl, 12.15; N, 4.80; O, 16.45; P, 10.62

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 380
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Crufomate; Crufomatum; M-1261; M 1261; M1261; Ruelene;

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

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.

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