ContaminantDB: Fenamiphos

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (9)XML

Record Information

Version

1.0

Creation Date

2013-04-25 07:56:51 UTC

Update Date

2026-03-25 19:26:18 UTC

Accession Number

CHEM002798

Identification

Common Name

Fenamiphos

Class

Small Molecule

Description

Fenamiphos is an organophosphate acetylcholinesterase inhibitor insecticide (nematicide) used to control a wide variety of nematode (round worm) pests. Nematodes can live as parasites on or within a plant. They may be free living or associated with cyst and root-knot formations in plants. Fenamiphos is used on a variety of plants including tobacco, cocoa, turf, bananas, pineapples, citrus and other fruit vines, and on some vegetables and grains. The compound is absorbed by the roots and is then transported throughout the plant. Fenamiphos, similar to other organophosphates, blocks the enzyme acetyl cholinesterase in the target pest. The enzyme regulates inter-cellular activity. The pesticide is also active against non-target invertebrates such as sucking insects and spider mites.

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Ester
Ether
Food Toxin
Insecticide
Metabolite
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Ethyl 3-methyl-4-(methylsulfanyl)phenyl (1-methylethyl)amidophosphate	ChEBI
Ethyl 3-methyl-4-(methylthio)phenyl isopropylphosphoramidate	ChEBI
Ethyl 4-(methylthio)-m-tolyl isopropylphosphoramidate	ChEBI
Isopropylamino-O-ethyl-(4-methylmercapto-3-methylphenyl)phosphate	ChEBI
Methaphenamiphos	ChEBI
Nemacur	ChEBI
Phenamiphos	ChEBI
Ethyl 3-methyl-4-(methylsulfanyl)phenyl (1-methylethyl)amidophosphoric acid	Generator
Ethyl 3-methyl-4-(methylsulphanyl)phenyl (1-methylethyl)amidophosphate	Generator
Ethyl 3-methyl-4-(methylsulphanyl)phenyl (1-methylethyl)amidophosphoric acid	Generator
Ethyl 3-methyl-4-(methylthio)phenyl isopropylphosphoramidic acid	Generator
Ethyl 4-(methylthio)-m-tolyl isopropylphosphoramidic acid	Generator
Isopropylamino-O-ethyl-(4-methylmercapto-3-methylphenyl)phosphoric acid	Generator
BAY sra 3886	HMDB
Ethyl 3-methyl-4-(methylthio)phenyl 1-methylethylphosphoramidate, 9ci	HMDB
Ethyl 3-methyl-4-(methylthio)phenyl isopropylamidophosphate	HMDB
Ethyl 4-(methylthio)m-tolyl isopropylphosphoroamidate	HMDB
Ethyl 4-methylthio-m-tolyl isopropylphosphoramidate, 8ci	HMDB
Ethyl-4-(methylthio)-m-tolyl isopropylphosphoramidate	HMDB
m-Cresol, 4-(methylthio)-, ethyl isopropylphosphoramidate	HMDB
Nemacur p	HMDB
Phenamifos sulfoxide	HMDB

Chemical Formula

C₁₃H₂₂NO₃PS

Average Molecular Mass

303.357 g/mol

Monoisotopic Mass

303.106 g/mol

CAS Registry Number

22224-92-6

IUPAC Name

{ethoxy[3-methyl-4-(methylsulfanyl)phenoxy]phosphoryl}(propan-2-yl)amine

Traditional Name

fenamiphos

SMILES

CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1

InChI Identifier

InChI=1S/C13H22NO3PS/c1-6-16-18(15,14-10(2)3)17-12-7-8-13(19-5)11(4)9-12/h7-10H,6H2,1-5H3,(H,14,15)

InChI Key

ZCJPOPBZHLUFHF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxy compounds

Direct Parent

Phenoxy compounds

Alternative Parents

Substituents

Phenoxy compound
Aryl thioether
Thiophenol ether
Phosphoric diester monoamide
Toluene
Alkylarylthioether
Organic phosphoric acid derivative
Phosphoric acid ester
Organic phosphoric acid amide
Sulfenyl compound
Thioether
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organic oxide
Organonitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phosphoramidate ester (CHEBI:38680 )
organophosphate insecticide (CHEBI:38680 )
organophosphate nematicide (CHEBI:38680 )
Phosphoramido insecticides (C18659 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

EC 3.1.1.7 (acetylcholinesterase) inhibitor

Chemical Roles

EC 3.1.1.7 (acetylcholinesterase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	49°C
Boiling Point	Not Available
Solubility	0.329 mg/mL at 20°C

Predicted Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	3.05	ALOGPS
logP	3.31	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	10.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.56 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	81.54 m³·mol⁻¹	ChemAxon
Polarizability	31.97 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w99-3890000000-69a80218e9aa4efa6a6e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0uxr-0390000000-27a48287856f24d6700c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0udi-2690000000-b722d2a9468435e12094	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0159-0090000000-d4a04a50c394cba968e1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-014i-0090000000-93cb423c35280cf6e7a7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0udi-0069000000-96078b842ad6c61e3d2a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0udi-5940000000-d70a968d944ba49dd1ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002r-1961000000-6a59a7d3929cb6c1f452	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1390000000-87f8471e9c820add2e93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-4900000000-26f0133ccf950f4cf465	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfs-4293000000-8d0f5c9a48d2dd05e238	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-2290000000-1a517cae8a7e665e46e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000b-7910000000-0b3532563157c053e6b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0129000000-c0cdb30129c325b775b6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0901000000-5cbc3028107c94f320c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0910000000-6fc9bd5a7c66c0afa14b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0imi-0193000000-f9f9fe0b8a64c4666f70	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00or-0390000000-41b52eaec89c60dbd994	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052u-6930000000-918bc9e7576314e226bb	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-8953000000-a605d591b58cd6b9edb9	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Fenamiphos is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Metabolism

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Symptoms

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0031787

FooDB ID

FDB008460

Phenol Explorer ID

Not Available

KNApSAcK ID