Bendiocarb
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Bendiocarb(F03960) |
| 2D Structure | |
| Description | Bendiocarb is a carbamate pesticide. Bendiocarb is a carbamate insecticide. 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. All bendiocarb-containing products in the United States were recently cancelled, after its manufacturers voluntarily chose to pull their products off the market, rather than conduct additional safety studies required by the EPA. In other countries, Bendiocarb is still used in homes, industrial plants, and food storage sites to control bedbugs, mosquitoes, flies, wasps, ants, fleas, cockroaches, silverfish, and ticks but can be used against a wide variety of insects as well as snails and slugs. It is one of 12 insecticides recommended by the World Health Organization for use in malaria control. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. |
| FRCD ID | F03960 |
| CAS Number | 22781-23-3 |
| PubChem CID | 2314 |
| Formula | C11H13NO4 |
| IUPAC Name | (2,2-dimethyl-1,3-benzodioxol-4-yl) N-methylcarbamate |
| InChI Key | XEGGRYVFLWGFHI-UHFFFAOYSA-N |
| InChI | InChI=1S/C11H13NO4/c1-11(2)15-8-6-4-5-7(9(8)16-11)14-10(13)12-3/h4-6H,1-3H3,(H,12,13) |
| Canonical SMILES | CC1(OC2=C(O1)C(=CC=C2)OC(=O)NC)C |
| Isomeric SMILES | CC1(OC2=C(O1)C(=CC=C2)OC(=O)NC)C |
| Synonyms |
Ficam W
Turcam
bendiocarb
22781-23-3
Bencarbate
Ficam
Multamat
Dycarb
Garvox
Niomil
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Benzodioxoles |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzodioxoles |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Benzodioxole - Ketal - Benzenoid - Carbamic acid ester - Carbonic acid derivative - Oxacycle - Acetal - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Organic nitrogen compound - Organopnictogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 223.228 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 2 |
| Complexity | 279 |
| Monoisotopic Mass | 223.084 |
| Exact Mass | 223.084 |
| XLogP | 1.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| 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+ | 0.8914 |
| Human Intestinal Absorption | HIA+ | 0.9952 |
| Caco-2 Permeability | Caco2- | 0.5209 |
| P-glycoprotein Substrate | Non-substrate | 0.7077 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7818 |
| Non-inhibitor | 0.7643 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9378 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4517 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7783 |
| CYP450 2D6 Substrate | Non-substrate | 0.7178 |
| CYP450 3A4 Substrate | Substrate | 0.5930 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5000 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8736 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8465 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8109 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8310 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5420 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9942 |
| Non-inhibitor | 0.9665 | |
| AMES Toxicity | Non AMES toxic | 0.5000 |
| Carcinogens | Non-carcinogens | 0.9139 |
| Fish Toxicity | High FHMT | 0.9091 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9758 |
| Honey Bee Toxicity | High HBT | 0.8538 |
| Biodegradation | Not ready biodegradable | 0.9554 |
| Acute Oral Toxicity | I | 0.7921 |
| Carcinogenicity (Three-class) | Non-required | 0.5159 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.7890 | LogS |
| Caco-2 Permeability | 1.0993 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.7787 | LD50, mol/kg |
| Fish Toxicity | 0.3758 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4372 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Other Vegetables | Japan | 0.05ppm | |||
| Other Poultry,Eggs | Japan | 0.05ppm | |||
| Chicken,Eggs | Japan | 0.05ppm | |||
| Other Poultry Animals,Edible Offal | Japan | 0.05ppm | |||
| Chicken,Edible Offal | Japan | 0.05ppm | |||
| Other Poultry Animals,Kidney | Japan | 0.05ppm | |||
| Chicken,Kidney | Japan | 0.05ppm | |||
| Other Poultry Animals,Liver | Japan | 0.05ppm | |||
| Chicken,Liver | Japan | 0.05ppm | |||
| Other Poultry Animals,Fat | Japan | 0.05ppm | |||
| Chicken,Fat | Japan | 0.05ppm | |||
| Other Poultry Animals,Muscle | Japan | 0.05ppm | |||
| Chicken,Muscle | Japan | 0.05ppm | |||
| Milk | Japan | 0.05ppm | |||
| Cattle,Edible Offal | Japan | 0.05ppm | |||
| Cattle,Kidney | Japan | 0.2ppm | |||
| Cattle,Liver | Japan | 0.05ppm | |||
| Cattle,Fat | Japan | 0.05ppm | |||
| Cattle,Muscle | Japan | 0.05ppm | |||
| Other Herbs | Japan | 0.05ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Bendiocarb induced histopathological and biochemical alterations in rat liver andpreventive role of vitamins C and E. | Environ Toxicol Pharmacol | 2017 Jan | 28013143 |
| DEET (N,N-diethyl-meta-toluamide)/PMD (para-menthane-3,8-diol) repellent-treated mesh increases Culicoides catches in light traps. | Parasitol Res | 2016 Sep | 27179956 |
| Influence of the agrochemicals used for rice and vegetable cultivation oninsecticide resistance in malaria vectors in southern Côte d'Ivoire. | Malar J | 2016 Aug 24 | 27553959 |
| Ensuring selectivity and sensitivity by timed- and ultra-selective reactionmonitoring during gas chromatography-tandem mass spectrometric determination ofpesticides. | J Chromatogr A | 2013 Nov 29 | 24161146 |
| Reagentless bidirectional lateral flow bioactive paper sensors for detection ofpesticides in beverage and food samples. | Anal Chem | 2009 Nov 1 | 19788278 |
| Analysis of phenoxyl-type N-methylcarbamate pesticide residues in vegetables bycapillary zone electrophoresis with pre-column hydrolysis and amperometricdetection. | J Chromatogr Sci | 2008 Aug | 18718137 |
| Development of simple and sensitive spectrophotometric method for thedetermination of bendiocarb in its formulations and environmental samples. | Environ Monit Assess | 2007 Apr | 16897507 |
| [Behavior of N-methylcarbamate pesticides during refinement processing of edible oils]. | J Oleo Sci | 2007 | 17898465 |
| Competitive degradation and detoxification of carbamate insecticides by membrane anodic Fenton treatment. | J Agric Food Chem | 2003 Aug 27 | 12926887 |
| Management of early-instar Japanese beetle (Coleoptera: Searabaeidae) infield-grown nursery crops. | J Econ Entomol | 2001 Oct | 11681678 |
| Lethal and sublethal effects of bendiocarb, halofenozide, and imidacloprid onHarpalus pennsylvanicus (Coleoptera: Carabidae) following different modes ofexposure in turfgrass. | J Econ Entomol | 2001 Feb | 11233134 |
| Surface partitioning studies of N-methylcarbamate-treated post-harvest cropsusing SFE-HPLC-postcolumn reaction-fluorescence. | Analyst | 1999 Mar | 10605888 |
| Susceptibilities of northern fowl mite, Ornithonyssus sylviarum (Acarina:Macronyssidae), and chicken mite, Dermanyssus gallinae (Acarina: Dermanyssidae), to selected acaricides. | Exp Appl Acarol | 1991 Dec | 1786744 |
| Liquid chromatographic determination of N-methylcarbamate insecticides and metabolites in crops. II. Analytical characteristics and residue findings. | J Assoc Off Anal Chem | 1985 Jul-Aug | 4030646 |
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 ]
- General Function:
- Platelet-derived growth factor binding
- Specific Function:
- Collagen type III occurs in most soft connective tissues along with type I collagen. Involved in regulation of cortical development. Is the major ligand of GPR56 in the developing brain and binding to GPR56 inhibits neuronal migration and activates the RhoA pathway by coupling GPR56 to GNA13 and possibly GNA12.
- Gene Name:
- COL3A1
- Uniprot ID:
- P02461
- Molecular Weight:
- 138564.005 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:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 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:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 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:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 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:
- Type iii transforming growth factor beta receptor binding
- Specific Function:
- Multifunctional protein that controls proliferation, differentiation and other functions in many cell types. Many cells synthesize TGFB1 and have specific receptors for it. It positively and negatively regulates many other growth factors. It plays an important role in bone remodeling as it is a potent stimulator of osteoblastic bone formation, causing chemotaxis, proliferation and differentiation in committed osteoblasts. Can promote either T-helper 17 cells (Th17) or regulatory T-cells (Treg) lineage differentiation in a concentration-dependent manner. At high concentrations, leads to FOXP3-mediated suppression of RORC and down-regulation of IL-17 expression, favoring Treg cell development. At low concentrations in concert with IL-6 and IL-21, leads to expression of the IL-17 and IL-23 receptors, favoring differentiation to Th17 cells.
- Gene Name:
- TGFB1
- Uniprot ID:
- P01137
- Molecular Weight:
- 44340.685 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 ]