Desmedipham
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Basic Info
Common Name | Desmedipham(F03986) |
2D Structure | |
Description | Desmedipham is a selective, systemic post-emergence herbicide of the phenyl carbamate and biscarbamate classes. 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. Desmedipham was developed by Schering AG and approved for use in the United States in 1970. It is commonly used in beet and strawberry crops to protect against weeds, often in comination with Phenmedipham under the trade names Betanal or Betamax. (L795) |
FRCD ID | F03986 |
CAS Number | 13684-56-5 |
PubChem CID | 24743 |
Formula | C16H16N2O4 |
IUPAC Name | [3-(ethoxycarbonylamino)phenyl] N-phenylcarbamate |
InChI Key | WZJZMXBKUWKXTQ-UHFFFAOYSA-N |
InChI | InChI=1S/C16H16N2O4/c1-2-21-15(19)18-13-9-6-10-14(11-13)22-16(20)17-12-7-4-3-5-8-12/h3-11H,2H2,1H3,(H,17,20)(H,18,19) |
Canonical SMILES | CCOC(=O)NC1=CC(=CC=C1)OC(=O)NC2=CC=CC=C2 |
Isomeric SMILES | CCOC(=O)NC1=CC(=CC=C1)OC(=O)NC2=CC=CC=C2 |
Synonyms | Schering 38107 DESMEDIPHAM 13684-56-5 Bentanex Betanex Synbetan D Betanal AM Betanal AM 11 Caswell No. 447AAA Desmediphame [ISO-French] |
Classifies | 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 - Phenoxy compound - 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 | 300.314 |
Hydrogen Bond Donor Count | 2 |
Hydrogen Bond Acceptor Count | 4 |
Rotatable Bond Count | 6 |
Complexity | 369 |
Monoisotopic Mass | 300.111 |
Exact Mass | 300.111 |
XLogP | 3.4 |
Formal Charge | 0 |
Heavy Atom Count | 22 |
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+ | 0.9197 |
Human Intestinal Absorption | HIA+ | 0.9859 |
Caco-2 Permeability | Caco2- | 0.5403 |
P-glycoprotein Substrate | Non-substrate | 0.7003 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.7048 |
Non-inhibitor | 0.7580 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9109 |
Distribution | ||
Subcellular localization | Mitochondria | 0.8907 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7562 |
CYP450 2D6 Substrate | Non-substrate | 0.7215 |
CYP450 3A4 Substrate | Non-substrate | 0.5741 |
CYP450 1A2 Inhibitor | Inhibitor | 0.7758 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.7233 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.8794 |
CYP450 2C19 Inhibitor | Inhibitor | 0.6994 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.8124 |
CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5058 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9423 |
Non-inhibitor | 0.8892 | |
AMES Toxicity | AMES toxic | 0.6482 |
Carcinogens | Non-carcinogens | 0.7928 |
Fish Toxicity | High FHMT | 0.9915 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9932 |
Honey Bee Toxicity | Low HBT | 0.5995 |
Biodegradation | Not ready biodegradable | 0.9305 |
Acute Oral Toxicity | IV | 0.6344 |
Carcinogenicity (Three-class) | Non-required | 0.4577 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -4.5676 | LogS |
Caco-2 Permeability | 0.8101 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.5264 | LD50, mol/kg |
Fish Toxicity | 0.8098 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.4980 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Other Cucurbits-Inedible Peel | Britain | 0.05mg/kg | |||
Other Solanacea | Britain | 0.05mg/kg | |||
Other Small Fruit & Berries (Other Than Wild) | Britain | 0.05mg/kg | |||
Watermelons | Britain | 0.05mg/kg | |||
Squashes | Britain | 0.05mg/kg | |||
Melons | Britain | 0.05mg/kg | |||
Other Cucurbits-Edible Peel | Britain | 0.05mg/kg | |||
Courgettes | Britain | 0.05mg/kg | |||
Gherkins | Britain | 0.05mg/kg | |||
Cucumbers | Britain | 0.05mg/kg | |||
Okra | Britain | 0.05mg/kg | |||
Aubergines | Britain | 0.05mg/kg | |||
Chili Peppers | Britain | 0.05mg/kg | |||
Peppers | Britain | 0.05mg/kg | |||
Tomatoes | Britain | 0.05mg/kg | |||
Other Bulb Vegetables | Britain | 0.05mg/kg | |||
Spring Onions | Britain | 0.05mg/kg | |||
Shallots | Britain | 0.05mg/kg | |||
Onions | Britain | 0.05mg/kg | |||
Garlic | Britain | 0.05mg/kg |
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
- General Function:
- Zinc ion binding
- Specific Function:
- Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
- Gene Name:
- NR1H4
- Uniprot ID:
- Q96RI1
- Molecular Weight:
- 55913.915 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Norepinephrine:sodium symporter activity
- Specific Function:
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A2
- Uniprot ID:
- P23975
- Molecular Weight:
- 69331.42 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]