Carbosulfan
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Basic Info
Common Name | Carbosulfan(F03977) |
2D Structure | |
Description | Carbosulfan 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 | F03977 |
CAS Number | 55285-14-8 |
PubChem CID | 41384 |
Formula | C20H32N2O3S |
IUPAC Name | (2,2-dimethyl-3H-1-benzofuran-7-yl) N-(dibutylamino)sulfanyl-N-methylcarbamate |
InChI Key | JLQUFIHWVLZVTJ-UHFFFAOYSA-N |
InChI | InChI=1S/C20H32N2O3S/c1-6-8-13-22(14-9-7-2)26-21(5)19(23)24-17-12-10-11-16-15-20(3,4)25-18(16)17/h10-12H,6-9,13-15H2,1-5H3 |
Canonical SMILES | CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C2)(C)C |
Isomeric SMILES | CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C2)(C)C |
Synonyms | Dibutylaminosulfenylcarbofuran Carbosulfan Marshal 55285-14-8 Posse Advantage Marshall Caswell No. 463C FMC 35001 UNII-V1DGN4AK6G |
Classifies | Pesticide |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organoheterocyclic compounds |
Class | Coumarans |
Subclass | Not available |
Intermediate Tree Nodes | Not available |
Direct Parent | Coumarans |
Alternative Parents | |
Molecular Framework | Aromatic heteropolycyclic compounds |
Substituents | Coumaran - Alkyl aryl ether - Benzenoid - Carbonic acid derivative - Oxacycle - Ether - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic heteropolycyclic compound |
Description | This compound belongs to the class of organic compounds known as coumarans. These are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 380.547 |
Hydrogen Bond Donor Count | 0 |
Hydrogen Bond Acceptor Count | 5 |
Rotatable Bond Count | 10 |
Complexity | 439 |
Monoisotopic Mass | 380.213 |
Exact Mass | 380.213 |
XLogP | 5.7 |
Formal Charge | 0 |
Heavy Atom Count | 26 |
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+ | 0.9413 |
Human Intestinal Absorption | HIA+ | 1.0000 |
Caco-2 Permeability | Caco2- | 0.5338 |
P-glycoprotein Substrate | Substrate | 0.7381 |
P-glycoprotein Inhibitor | Inhibitor | 0.6047 |
Non-inhibitor | 0.9409 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.7810 |
Distribution | ||
Subcellular localization | Mitochondria | 0.5151 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.6020 |
CYP450 2D6 Substrate | Non-substrate | 0.7408 |
CYP450 3A4 Substrate | Substrate | 0.6885 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.6945 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.6559 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.7970 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.5794 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.8879 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6884 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8673 |
Non-inhibitor | 0.6665 | |
AMES Toxicity | Non AMES toxic | 0.6210 |
Carcinogens | Non-carcinogens | 0.7615 |
Fish Toxicity | High FHMT | 0.9963 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9807 |
Honey Bee Toxicity | High HBT | 0.6269 |
Biodegradation | Not ready biodegradable | 0.9934 |
Acute Oral Toxicity | II | 0.7172 |
Carcinogenicity (Three-class) | Non-required | 0.6052 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -4.2568 | LogS |
Caco-2 Permeability | 1.3081 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 3.8415 | LD50, mol/kg |
Fish Toxicity | 1.0138 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.6714 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Mitsuba | Japan | 1ppm | |||
Celery | Japan | 1ppm | |||
Parsley | Japan | 1ppm | |||
Parsnip | Japan | 1ppm | |||
Carrot | Japan | 1ppm | |||
Huckleberry | Japan | 0.2ppm | |||
Cranberry | Japan | 0.2ppm | |||
Blueberry | Japan | 0.2ppm | |||
Blackberry | Japan | 0.2ppm | |||
Raspberry | Japan | 0.2ppm | |||
Cherry | Japan | 0.2ppm | |||
Mume Plum | Japan | 0.2ppm | |||
Milk & Dairy Produce | Britain | 0.05mg/kg | |||
Meat, Fat & Preparations Of Meat | Britain | 0.05mg/kg | |||
Other Cereals Do Not Include Rice | Britain | 0.05mg/kg | |||
Rice | Britain | 0.05mg/kg | |||
Millet | Britain | 0.05mg/kg | |||
Buckwheat | Britain | 0.05mg/kg | |||
Maize | Britain | 0.05mg/kg | |||
Triticale | Britain | 0.05mg/kg |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Residue behavior and dietary intake risk assessment of carbosulfan and its metabolites in cucumber. | Regul Toxicol Pharmacol | 2018 Jun | 29601912 |
Self-Reported Symptoms and Pesticide Use among Farm Workers in Arusha, NorthernTanzania: A Cross Sectional Study. | Toxics | 2017 Sep 27 | 29051456 |
Electrochemical acetylcholinesterase biosensor based on ZnO nanocuboids modified platinum electrode for the detection of carbosulfan in rice. | Biosens Bioelectron | 2016 Mar 15 | 26562329 |
A comparative study on toxicity induced by carbosulfan and malathion in Wistar rat liver and spleen. | Pestic Biochem Physiol | 2015 Oct | 26453226 |
Mutagenic and genotoxic effects of carbosulfan in freshwater fish Channapunctatus (Bloch) using micronucleus assay and alkaline single-cell gelelectrophoresis. | Food Chem Toxicol | 2010 Jan | 19818828 |
Persistence and nematicidal efficacy of carbosulfan, cadusafos, phorate, andtriazophos in soil and uptake by chickpea and tomato crops under tropicalconditions. | J Agric Food Chem | 2010 Feb 10 | 20085277 |
Determination of pesticide residues in integrated pest management andnonintegrated pest management samples of apple (Malus pumila Mill.). | J Agric Food Chem | 2009 Dec 9 | 19904932 |
Liquid chromatography quadrupole time-of-flight mass spectrometry analysis ofcarbosulfan, carbofuran, 3-hydroxycarbofuran, and other metabolites in food. | Anal Chem | 2007 Feb 15 | 17241092 |
[Behavior of N-methylcarbamate pesticides during refinement processing of edible oils]. | J Oleo Sci | 2007 | 17898465 |
An approach for IPM program to control sucking pests infesting garden bean plants(Phaseolus vulgaris L.) in Egypt. | Commun Agric Appl Biol Sci | 2007 | 18399490 |
Supercritical fluid extraction of the pesticides carbosulfan and imidaclopridfrom process dust waste. | J Agric Food Chem | 2000 Nov | 11087452 |
Targets
- 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:
- 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
- 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 ]