Tebuthiuron
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Basic Info
| Common Name | Tebuthiuron(F05142) |
| 2D Structure | |
| Description | Tebuthiuron is a nonselective broad spectrum herbicide of the urea class. It is used in a number of herbicides manufactured by Dow AgroSciences, and is sold under several trade names, depending on the formulation. It is used to control weeds, woody and herbaceous plants, and sugar cane. It is absorbed by the roots and transported to the leaves, where it inhibits photosynthesis. |
| FRCD ID | F05142 |
| CAS Number | 34014-18-1 |
| PubChem CID | 5383 |
| Formula | C9H16N4OS |
| IUPAC Name | 1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea |
| InChI Key | HBPDKDSFLXWOAE-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H16N4OS/c1-9(2,3)6-11-12-8(15-6)13(5)7(14)10-4/h1-5H3,(H,10,14) |
| Canonical SMILES | CC(C)(C)C1=NN=C(S1)N(C)C(=O)NC |
| Isomeric SMILES | CC(C)(C)C1=NN=C(S1)N(C)C(=O)NC |
| Synonyms |
tebuthiuron
34014-18-1
Spike
Graslan
Perflan
Brulan
Tiurolan
Prefmid
Tebulan
Brush bullet
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Azoles |
| Subclass | Thiadiazoles |
| Intermediate Tree Nodes | Aminothiadiazoles - 2-amino-1,3,4-thiadiazoles |
| Direct Parent | 1,3,4-thiadiazol-2-ylureas |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | 1,3,4-thiadiazol-2-ylurea - Heteroaromatic compound - Urea - Carbonic acid derivative - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as 1,3,4-thiadiazol-2-ylureas. These are aromatic compounds containing a 1,3,4-thiadiazole ring, which is substituted at the 2-position with urea. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 228.314 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 2 |
| Complexity | 241 |
| Monoisotopic Mass | 228.104 |
| Exact Mass | 228.104 |
| XLogP | 1.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| 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+ | 0.9422 |
| Human Intestinal Absorption | HIA+ | 0.9575 |
| Caco-2 Permeability | Caco2- | 0.5106 |
| P-glycoprotein Substrate | Non-substrate | 0.7812 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7817 |
| Non-inhibitor | 0.8945 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9150 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6576 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7966 |
| CYP450 2D6 Substrate | Non-substrate | 0.8131 |
| CYP450 3A4 Substrate | Non-substrate | 0.5360 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5000 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6745 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9566 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7757 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9489 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6978 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9830 |
| Non-inhibitor | 0.8288 | |
| AMES Toxicity | Non AMES toxic | 0.7243 |
| Carcinogens | Non-carcinogens | 0.7400 |
| Fish Toxicity | High FHMT | 0.9160 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7948 |
| Honey Bee Toxicity | Low HBT | 0.7752 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7954 |
| Carcinogenicity (Three-class) | Danger | 0.3995 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.6594 | LogS |
| Caco-2 Permeability | 1.3998 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.5185 | LD50, mol/kg |
| Fish Toxicity | 1.4854 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3930 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Mume Plum | Japan | 0.02ppm | |||
| Milk | Japan | 0.3ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 2ppm | |||
| Pig,Edible Offal | Japan | 2ppm | |||
| Cattle,Edible Offal | Japan | 2ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 2ppm | |||
| Pig,Kidney | Japan | 2ppm | |||
| Cattle,Kidney | Japan | 2ppm | |||
| Other Terrestrial Mammals,Liver | Japan | 2ppm | |||
| Pig,Liver | Japan | 2ppm | |||
| Cattle,Liver | Japan | 2ppm | |||
| Other Terrestrial Mammals,Fat | Japan | 2ppm | |||
| Pig,Fat | Japan | 2ppm | |||
| Tomato | Japan | 0.02ppm | |||
| Other Umbelliferous Vegetables | Japan | 0.02ppm | |||
| Mitsuba | Japan | 0.02ppm | |||
| Celery | Japan | 0.02ppm | |||
| Parsley | Japan | 0.02ppm | |||
| Parsnip | Japan | 0.02ppm | |||
| Carrot | Japan | 0.02ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| How benthic diatoms within natural communities respond to eight common herbicides with different modes of action. | Sci Total Environ | 2016 Jul 1 | 27037885 |
Targets
- 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:
- Transferase activity
- Specific Function:
- Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
- Gene Name:
- CD38
- Uniprot ID:
- P28907
- Molecular Weight:
- 34328.145 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 ]
- Gene Name:
- CCL2
- Uniprot ID:
- P13500
- Molecular Weight:
- 11024.87 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:
- Transmembrane signaling receptor activity
- Specific Function:
- Involved in lymphocyte proliferation and functions as a signal transmitting receptor in lymphocytes, natural killer (NK) cells, and platelets.
- Gene Name:
- CD69
- Uniprot ID:
- Q07108
- Molecular Weight:
- 22559.25 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 ]