Terbucarb
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Basic Info
| Common Name | Terbucarb(F04031) |
| 2D Structure | |
| Description | Terbucarb 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 | F04031 |
| CAS Number | 1918-11-2 |
| PubChem CID | 15967 |
| Formula | C17H27NO2 |
| IUPAC Name | (2,6-ditert-butyl-4-methylphenyl) N-methylcarbamate |
| InChI Key | PNRAZZZISDRWMV-UHFFFAOYSA-N |
| InChI | InChI=1S/C17H27NO2/c1-11-9-12(16(2,3)4)14(20-15(19)18-8)13(10-11)17(5,6)7/h9-10H,1-8H3,(H,18,19) |
| Canonical SMILES | CC1=CC(=C(C(=C1)C(C)(C)C)OC(=O)NC)C(C)(C)C |
| Isomeric SMILES | CC1=CC(=C(C(=C1)C(C)(C)C)OC(=O)NC)C(C)(C)C |
| Synonyms |
Hercules 9573
Terbucarb
Terbutol
azak
Mbpmc
Terbucarb [ISO]
AZAC
AZAR
1918-11-2
Caswell No. 294
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Phenyl methylcarbamates |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenyl methylcarbamates |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Phenyl methylcarbamate - Phenylpropane - Phenoxy compound - Toluene - 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 phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 277.408 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 4 |
| Complexity | 314 |
| Monoisotopic Mass | 277.204 |
| Exact Mass | 277.204 |
| XLogP | 5.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 20 |
| 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+ | 0.9461 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.7461 |
| P-glycoprotein Substrate | Non-substrate | 0.7934 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9127 |
| Non-inhibitor | 0.9740 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9135 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7730 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7549 |
| CYP450 2D6 Substrate | Substrate | 0.6472 |
| CYP450 3A4 Substrate | Substrate | 0.6497 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5862 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8677 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8718 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7733 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8277 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6860 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9775 |
| Non-inhibitor | 0.9520 | |
| AMES Toxicity | Non AMES toxic | 0.5412 |
| Carcinogens | Non-carcinogens | 0.8255 |
| Fish Toxicity | High FHMT | 0.8349 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9011 |
| Honey Bee Toxicity | High HBT | 0.8339 |
| Biodegradation | Not ready biodegradable | 0.9551 |
| Acute Oral Toxicity | IV | 0.6146 |
| Carcinogenicity (Three-class) | Non-required | 0.6109 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.3153 | LogS |
| Caco-2 Permeability | 1.7066 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0794 | LD50, mol/kg |
| Fish Toxicity | 0.4643 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4564 | pIGC50, ug/L |
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