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Crufomate
Names
	IUPAC name 4-tert-butyl-2-chlorophenyl methyl methylphosphoramidate
	Other names Dowco 132; Montrel; Ruelene; crufomat; phosphoramidic acid, 4-tert-butyl-2-chlorophenyl-phosphoramidate; Rulene 25E
Identifiers
CAS Number	299-86-5 ;
RTECS number	TB3850000;
UNII	V82Q65924L ;
UN number	2783
Properties
Chemical formula	C12H19ClNO3P
Molar mass	291.71 g/mol
Appearance	white crystals
Density	1.5 g/mL
Melting point	60-60.5°C
Vapor pressure	0.106 Pa at 25°C
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Crufomate produces toxic fumes and reacts with strong acids and bases.
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Crufomate is a white solid at room temperature, but it is also very soluble with most organic solvents. It is found as a yellow oil in pesticide residues of food. Also, crufomate is monitored by food and agricultural organizations for levels of toxicity in animals and humans. It is found in an insecticide for lice, cattle grubs, and horn flies.

Environmental Effects

Crufomate was once produced and used as Ruelene, an insecticide used in controlling cattle grub. It has more recently though become obsolete as a result of more efficient and environmentally friendly alternatives being discovered. At the time though, Ruelene exposure to humans was most prevalently found in the release of the toxin into the atmosphere. As such, Ruelene exposure exists mostly in the vapor phase, as opposed to within the soil. Humans can take in this toxin through inhalation, skin contact, and ingestion of contaminated food.

Properties

The melting point at the white solid form is at 62-62.5°C, but as the recrystallized product, the melting temperature is 52.5-59.2°C. It is very unstable in a strong acid or strong base. At room temperature, this chemical is very soluble. Several concentrations of crufomate is created for direct use or for dilution application.

Hazards

Crufomate is combustible. This is prevented by not having open flames. If inhaled, symptoms are dizziness, sweating, nausea, vomiting, etc. If ingested, this can cause abdominal cramps, diarrhea, nausea, vomiting, etc. If it comes in contact with the eyes, redness or pain can occur. If there is contact with the skin, crufomate may be absorbed which would cause redness. To prevent these hazards from occurring it is important to maintain proper protection such as: protective gloves (for your skin), goggles or a form of eye protection, and a face mask to avoid inhaling small particles. To prevent ingestion, simply refrain from eating, drinking, or smoking when dealing with Crufomate.

Structure

Crufomate has the formula C12H19ClNO3P. It consists of an cholorphenyl group with the chlorine on the second carbon. Attached is a methylphosphoramidate on the 1 carbon, and a tert-butyl on the 4 carbon of the chlorophenyl.

Toxicity

After oral doses given to sheep, 5-15% were not excreted. The compound that remained was made of inorganic phosphate that was incorporated into the bone. It was also fed to hens for seven days, and residue was found in egg yolks 3-5 days after ceasing doses. Along with egg yolks, residue will also be found in milk. Because this compound is also found in pesticides, it can have harmful effects to the body because of the inactivation of the esterase enzyme activity. The pesticide can also subsequently affect receptors of acetylcholine. This compound affects insects and humans by the phosphorylation of an esterase enzyme at nerve endings. After too much compound consumption in humans, tension, anxiety, restlessness, insomnia, and other symptoms might occur. Those under 18 years old, expecting mothers, alcoholics, and those who work with toxic chemicals are at higher risk for the effects of the pesticide.

References

1. International Programme on Chemical Safety. "ICSC 1143 - CRUFOMATE." ICSC 1143 - CRUFOMATE. European Commission, 2012. Web. 31 Oct. 2012. <http://www.inchem.org/documents/icsc/icsc/eics1143.htm>.

2. International Programme on Chemical Safety. "International Chemical Safety Cards." CRUFOMATE. European Communities, 1993. Web. 31 Oct. 2012. <http://actrav.itcilo.org/actrav-english/telearn/osh/ic/299865.htm>.

3. National Center for Biotechnology Information. "Crufomate - Compound Summary." Pub Chem Compound. U.S. National Library of Medicine, n.d. Web. 31 Oct. 2012. <http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?q=all&cid=9300#x332>.

4. Occupational Safety & Health Administration. "Sampling and Analytical Methods: Crufomate, PV2015." Sampling and Analytical Methods:Crufomate, PV2015. U.S. Department of Labor, n.d. Web. 31 Oct. 2012. <http://www.osha.gov/dts/sltc/methods/partial/pv2015/2015.html>.

5. U.S. Secretary of Commerce. "Crufomate." Crufomate. NIST Standard Reference Data, 2011. Web. 01 Nov. 2012. <http://webbook.nist.gov/cgi/cbook.cgi?ID=C299865>.

6. WHO Expert Committee on Pesticide Residues. "120. Crufomate (FAO/PL:1968/M/9/1)." 120. Crufomate (FAO/PL:1968/M/9/1). Joint Meeting of the FAO Working Party of Experts, 1969. Web. 31 Oct. 2012. <http://www.inchem.org/documents/jmpr/jmpmono/v068pr11.htm>.

7. Wood, Alan. "Crufomate." Data Sheet. ISO Technical Committee 81, July 2012. Web. 01 Nov. 2012. <http://www.alanwood.net/pesticides/crufomate.html>.