Propham
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Basic Info
Common Name | Propham(F04024) |
2D Structure | |
Description | Propham is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (L795) |
FRCD ID | F04024 |
CAS Number | 122-42-9 |
PubChem CID | 24685 |
Formula | C10H13NO2 |
IUPAC Name | propan-2-yl N-phenylcarbamate |
InChI Key | VXPLXMJHHKHSOA-UHFFFAOYSA-N |
InChI | InChI=1S/C10H13NO2/c1-8(2)13-10(12)11-9-6-4-3-5-7-9/h3-8H,1-2H3,(H,11,12) |
Canonical SMILES | CC(C)OC(=O)NC1=CC=CC=C1 |
Isomeric SMILES | CC(C)OC(=O)NC1=CC=CC=C1 |
Synonyms | Prophame Propham Isopropyl phenylcarbamate 122-42-9 Isopropyl N-phenylcarbamate Triherbide Agermin Collavin Tuberit Tuberite |
Classifies | Veterinary Drug Pesticide |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Benzenoids |
Class | Benzene and substituted derivatives |
Subclass | Phenylcarbamic acid esters |
Intermediate Tree Nodes | Not available |
Direct Parent | Phenylcarbamic acid esters |
Alternative Parents | |
Molecular Framework | Aromatic homomonocyclic compounds |
Substituents | Phenylcarbamic acid ester - Carbamic acid ester - Carbonic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic homomonocyclic compound |
Description | This compound belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 179.219 |
Hydrogen Bond Donor Count | 1 |
Hydrogen Bond Acceptor Count | 2 |
Rotatable Bond Count | 3 |
Complexity | 162 |
Monoisotopic Mass | 179.095 |
Exact Mass | 179.095 |
XLogP | 2.6 |
Formal Charge | 0 |
Heavy Atom Count | 13 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9858 |
Human Intestinal Absorption | HIA+ | 1.0000 |
Caco-2 Permeability | Caco2+ | 0.7778 |
P-glycoprotein Substrate | Non-substrate | 0.8769 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9210 |
Non-inhibitor | 0.8707 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9332 |
Distribution | ||
Subcellular localization | Mitochondria | 0.7418 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7818 |
CYP450 2D6 Substrate | Non-substrate | 0.6347 |
CYP450 3A4 Substrate | Non-substrate | 0.5209 |
CYP450 1A2 Inhibitor | Inhibitor | 0.7204 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.8452 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9267 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.8380 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9681 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6105 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9645 |
Non-inhibitor | 0.9599 | |
AMES Toxicity | Non AMES toxic | 0.7174 |
Carcinogens | Non-carcinogens | 0.6233 |
Fish Toxicity | High FHMT | 0.8744 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9035 |
Honey Bee Toxicity | High HBT | 0.6172 |
Biodegradation | Not ready biodegradable | 0.5915 |
Acute Oral Toxicity | III | 0.7990 |
Carcinogenicity (Three-class) | Non-required | 0.6706 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -2.1486 | LogS |
Caco-2 Permeability | 1.7896 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.2222 | LD50, mol/kg |
Fish Toxicity | 1.5073 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.1733 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Aril spices | 0870000 | European Union | 0.05* | 30/12/2015 | |
Mace | 0870010 | European Union | 0.05* | 30/12/2015 | |
Bud spices | 0850000 | European Union | 0.05* | 30/12/2015 | |
Cloves (Cassia buds, Cassia buds, Cassia buds,) | 0850010 | European Union | 0.05* | 30/12/2015 | |
Capers (Nasturtium pods, Nasturtium pods,) | 0850020 | European Union | 0.05* | 30/12/2015 | |
Others (2) | 0850990 | European Union | 0.05* | 30/12/2015 | |
Flower pistil spices | 0860000 | European Union | 0.05* | 30/12/2015 | |
Saffron | 0860010 | European Union | 0.05* | 30/12/2015 | |
Others (2) | 0860990 | European Union | 0.05* | 30/12/2015 | |
Others (2) | 0870990 | European Union | 0.05* | 30/12/2015 | |
(a) swine (Wild boar (farmed),) | 1011000 | European Union | 0.01* | 30/12/2015 | |
Muscle | 1011010 | European Union | 0.01* | 30/12/2015 | |
Fat | 1011020 | European Union | 0.01* | 30/12/2015 | |
Liver | 1011030 | European Union | 0.01* | 30/12/2015 | |
Kidney | 1011040 | European Union | 0.01* | 30/12/2015 | |
Edible offals (other than liver and kidney) | 1011050 | European Union | 0.01* | 30/12/2015 | |
Others (2) | 1011990 | European Union | 0.01* | 30/12/2015 | |
Muscle | 1012010 | European Union | 0.01* | 30/12/2015 | |
Fat | 1012020 | European Union | 0.01* | 30/12/2015 | |
Liver | 1012030 | European Union | 0.01* | 30/12/2015 |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Pesticide residues in propolis from Spain and Chile. An approach using nearinfrared spectroscopy. | Talanta | 2017 Apr 1 | 28153295 |
A pilot survey of 39 Victorian WWTP effluents using a high speed luminescent umu test in conjunction with a novel GC-MS-database technique for automaticidentification of micropollutants. | Water Sci Technol | 2012 | 22766865 |
Determination of plant resistance to carbamate herbicidal compounds inhibitingcell division and early growth by seed and plantlets bioassays. | Nat Protoc | 2006 | 17406469 |
Determination of imidacloprid, metalaxyl, myclobutanil, propham, andthiabendazole in fruits and vegetables by liquid chromatography-atmosphericpressure chemical ionization-mass spectrometry. | Fresenius J Anal Chem | 2001 Sep | 11678189 |
Comparison of an HPTLC and an HPLC procedure for the determination ofchlorpropham, propham and thiabendazole residues in potatoes. | Food Addit Contam | 1991 Sep-Oct | 1818834 |
Targets
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
References
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
- General Function:
- Identical protein binding
- Specific Function:
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name:
- BCHE
- Uniprot ID:
- P06276
- Molecular Weight:
- 68417.575 Da
- Mechanism of Action:
- Like the organophosphates, their mode of action is inhibition of cholinesterase enzymes, affecting nerve impulse transmission.
References
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088