 | |
| Names | |
|---|---|
| Preferred IUPAC name O-(4-Bromo-2-chlorophenyl)O-ethylS-propyl phosphorothioate | |
| Other names Phosphorothioic acid, O-(4-bromo-2-chlorophenyl)O-ethylS-propyl ester | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.050.215 |
| UNII | |
| |
| |
| Properties | |
| C11H15BrClO3PS | |
| Molar mass | 373.63 g·mol−1 |
| Appearance | Pale yellow to amber liquid |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Profenofos is anorganophosphateinsecticide. It is aliquid with a pale yellow to amber color and agarlic-likeodor.[1] It was first registered in the United States in 1982.[3]: 1 As of 2015, it was not approved in theEuropean Union.[4]
Profenofos can be used on a variety of crops includingcotton andvegetables such asmaize,potato,soybean, andsugar beet.[5]: 404 In the United States it is used exclusively on cotton and is primarily used againstlepidopteran insects.[3]: 1
Mixed withphoxim,cypermethrin, beta-cypermethrinimidacloprid anddeltamethrin, profenofos can be used against Cotton MealyBug,cabbage caterpillar,Plutella xylostella andasparagus caterpillars, as well as againstwheat andcabbage aphids.[citation needed]
Like other organophosphates, the profenofosmechanism of action is via the inhibition of theacetylcholinesteraseenzyme. Although it is used in the form of aracemate, the S(-)isomer is a more potent inhibitor.[5]: 404
Profenofos can besynthesized by reactingphosphorus oxychloride withsodium ethoxide and sodium 1-propanethiolate, followed by treatment with 4-bromo-2-chlorophenol.[6]: 332
A 2007World Health Organization report found no adverse effects to workers of routine exposure to profenofos and noteratogenicity orcarcinogenicity.[5]: 435–8
Based on a study of patients poisoned with profenofos and its close chemical relativeprothiofos, the compound has been described as "of moderately severetoxicity", causingrespiratory failure. Differences in chemical structure that distinguish these two compounds from more common organophosphate pesticides - namely, the presence of theS-alkyl group on thephosphorus atom where most OP compounds possess amethoxy orethoxy group - underlie differences in their behavior asacetylcholinesteraseenzymeinhibitors compared to the rest of the OP class.[7]
In one study of a patient who died of profenofos poisoning, the majormetabolites of profenofos were identified as des-S-propylated profenofos, twoisomers of despropylated propenofos, and desethylated propenofos.[8] A downstream, nontoxic metabolite, 4-bromo-2-chlorophenol, has been proposed asbiomarker for exposure.[9]
A United StatesEnvironmental Protection Agency report identified profenofos as toxic tobirds, smallmammals,bees,fish, andaquatic invertebrates, noting severalfish kill incidents in which profenofos exposure, primarily due torunoff, was implicated as a probable cause.[3]: 2–3
