Tebufenozide
(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 | Tebufenozide(F05139) |
| 2D Structure | |
| Description | Tebufenozide is an insecticide that acts as a molting hormone. It is an agonist of ecdysone that causes premature molting in larvae. It is primarily used against caterpillar pests. |
| FRCD ID | F05139 |
| CAS Number | 112410-23-8 |
| PubChem CID | 91773 |
| Formula | C22H28N2O2 |
| IUPAC Name | N-tert-butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide |
| InChI Key | QYPNKSZPJQQLRK-UHFFFAOYSA-N |
| InChI | InChI=1S/C22H28N2O2/c1-7-17-8-10-18(11-9-17)20(25)23-24(22(4,5)6)21(26)19-13-15(2)12-16(3)14-19/h8-14H,7H2,1-6H3,(H,23,25) |
| Canonical SMILES | CCC1=CC=C(C=C1)C(=O)NN(C(=O)C2=CC(=CC(=C2)C)C)C(C)(C)C |
| Isomeric SMILES | CCC1=CC=C(C=C1)C(=O)NN(C(=O)C2=CC(=CC(=C2)C)C)C(C)(C)C |
| Synonyms |
N-tert-Butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide
Tebufenozide
112410-23-8
Tebufenozide [ISO]
Confirm
UNII-TNN5MI5EKF
RH-5992
CHEBI:38452
HSDB 7050
N'-(t-Butyl)-N'-(3,5-dimethylbenzoyl)-N-(4-ethylbenzoyl)hydrazine
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzoic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzoic acids and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Benzoic acid or derivatives - M-xylene - Xylene - Benzoyl - Carboxylic acid hydrazide - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzoic acids and derivatives. These are organic compounds containing a carboxylic acid substituent attached to a benzene ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 352.478 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 4 |
| Complexity | 479 |
| Monoisotopic Mass | 352.215 |
| Exact Mass | 352.215 |
| XLogP | 3.9 |
| 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+ | 0.9857 |
| Human Intestinal Absorption | HIA+ | 0.9945 |
| Caco-2 Permeability | Caco2+ | 0.7344 |
| P-glycoprotein Substrate | Non-substrate | 0.7304 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.5923 |
| Non-inhibitor | 0.8720 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9273 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8574 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7413 |
| CYP450 2D6 Substrate | Non-substrate | 0.8548 |
| CYP450 3A4 Substrate | Non-substrate | 0.5000 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7837 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5910 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9079 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5225 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7960 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7020 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9889 |
| Non-inhibitor | 0.9156 | |
| AMES Toxicity | Non AMES toxic | 0.9147 |
| Carcinogens | Carcinogens | 0.7108 |
| Fish Toxicity | High FHMT | 0.9635 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9969 |
| Honey Bee Toxicity | Low HBT | 0.8384 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | IV | 0.6248 |
| Carcinogenicity (Three-class) | Danger | 0.3716 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.7355 | LogS |
| Caco-2 Permeability | 1.5522 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.1805 | LD50, mol/kg |
| Fish Toxicity | 0.5760 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7348 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Other Poultry Animals,Edible Offal | Japan | 0.02ppm | |||
| Other Terrestrial Mammals,Muscle | Japan | 0.02ppm | |||
| Blackberry | Japan | 1ppm | |||
| Apricot | Japan | 1ppm | |||
| Nectarine | Japan | 0.5ppm | |||
| Peach | Japan | 0.5ppm | |||
| Loquat | Japan | 1ppm | |||
| Quince | Japan | 1ppm | |||
| Pear | Japan | 1ppm | |||
| Japanese Pear | Japan | 1ppm | |||
| Other Citrus Fruits | Japan | 2ppm | |||
| Lime | Japan | 2ppm | |||
| Grapefruit | Japan | 2ppm | |||
| Orange(Including Navel Orange) | Japan | 2ppm | |||
| Lemon | Japan | 2ppm | |||
| Citrus Natsudaidai,Whole | Japan | 2ppm | |||
| Unshu Orange,Pulp | Japan | 2ppm | |||
| Other Vegetables | Japan | 20ppm | |||
| Ginger | Japan | 0.02ppm | |||
| Spinach | Japan | 10ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Assessment of field re-entry exposure to pesticides: A dislodgeable foliarresidue study. | Sci Total Environ | 2017 Oct 15 | 28432907 |
| Effect of processing on the disappearance of pesticide residues in fresh-cutlettuce: Bioavailability and dietary risk. | J Environ Sci Health B | 2017 Dec 2 | 28949798 |
| Dissipation and metabolism of tebufenozide in cabbage and soil under open fieldconditions in South China. | Ecotoxicol Environ Saf | 2016 Dec | 27636325 |
| A Fundamental Step in IPM on Grapevine: Evaluating the Side Effects of Pesticideson Predatory Mites. | Insects | 2015 Oct 9 | 26466903 |
| The molecular and physiological impact of bisphenol A in Sesamia nonagrioides (Lepidoptera: Noctuidae). | Ecotoxicology | 2015 Mar | 25492584 |
| Fate of three insect growth regulators (IGR) insecticides (flufenoxuron,lufenuron and tebufenozide) in grapes following field application and through thewine-making process. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2011Feb | 21318916 |
| Isoforms of the heteropteran Nezara viridula ecdysone receptor: proteincharacterisation, RH5992 insecticide binding and homology modelling. | Pest Manag Sci | 2011 Nov | 21594962 |
| Synthesis and insecticidal activity of N-tert-butyl-N,N'-diacylhydrazinescontaining 1,2,3-thiadiazoles. | J Agric Food Chem | 2011 Jan 26 | 21166420 |
| Residue analysis of four diacylhydrazine insecticides in fruits and vegetables byQuick, Easy, Cheap, Effective, Rugged, and Safe (QuEChERS) method usingultra-performance liquid chromatography coupled to tandem mass spectrometry. | Anal Bioanal Chem | 2011 Aug | 21660414 |
| Activity of broad-spectrum and reduced-risk insecticides on various life stages of cranberry fruitworm (Lepidoptera: Pyralidae) in highbush blueberry. | J Econ Entomol | 2010 Oct | 21061972 |
| Reducing the impact of pesticides on biological control in Australian vineyards: pesticide mortality and fecundity effects on an indicator species, the predatory mite Euseius victoriensis (Acari: Phytoseiidae). | J Econ Entomol | 2010 Dec | 21309226 |
| Multiple pesticide analysis in wine by MEKC combined with solid-phasemicroextraction and sample stacking. | Electrophoresis | 2007 Nov | 17957661 |
| Ovicidal and larvicidal effectiveness of insecticides applied by dipping appleson the small fruit tortrix Grapholita lobarzewskii. | Pest Manag Sci | 2007 Jul | 17503401 |
| Agrichemical impact on growth and survival of non-target apple phyllospheremicroorganisms. | Can J Microbiol | 2007 Jan | 17496949 |
| Pesticide analysis in rose wines by micellar electrokinetic chromatography. | J Sep Sci | 2007 Dec | 18027361 |
| Novel life stage targets against plum curculio, Conotrachelus nenuphar (Herbst), in apple integrated pest management. | Pest Manag Sci | 2007 Aug | 17575566 |
| Stage-specific control of grape berry moth, Endopiza viteana (Clemens)(Lepidoptera: Tortricidae), by selective and broad-spectrum insecticides. | J Econ Entomol | 2005 Apr | 15889733 |
| Synthesis and insecticidal evaluation of novel N-oxalyl derivatives oftebufenozide. | J Agric Food Chem | 2004 Nov 3 | 15506810 |
| Toxicity and residual activity of methoxyfenozide and tebufenozide to codlingmoth (Lepidoptera: Tortricidae) and oriental fruit moth (Lepidoptera:Tortricidae). | J Econ Entomol | 2004 Aug | 15384347 |
| Some ecological implications of a neem (azadirachtin) insecticide disturbance to zooplankton communities in forest pond enclosures. | Aquat Toxicol | 2004 Apr 28 | 15063074 |
Targets
- General Function:
- Receptor activity
- Specific Function:
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
- Gene Name:
- CHRM3
- Uniprot ID:
- P20309
- Molecular Weight:
- 66127.445 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:
- Vitamin d3 25-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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 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:
- 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:
- 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:
- Transporter activity
- Specific Function:
- Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
- Gene Name:
- ABCB11
- Uniprot ID:
- O95342
- Molecular Weight:
- 146405.83 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:
- Vitamin d 24-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.
- Gene Name:
- CYP1A1
- Uniprot ID:
- P04798
- Molecular Weight:
- 58164.815 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:
- 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:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- 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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 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:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 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 binding
- Specific Function:
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
- Gene Name:
- UGT1A1
- Uniprot ID:
- P22309
- Molecular Weight:
- 59590.91 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:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
- Gene Name:
- PPARG
- Uniprot ID:
- P37231
- Molecular Weight:
- 57619.58 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 ]