Methoxyfenozide
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Basic Info
| Common Name | Methoxyfenozide(F05104) |
| 2D Structure | |
| Description | Methoxyfenozide ia a diacylhydrazine insecticide that binds with very high affinity to the ecdysone receptor complex where it functions as a potent agonist, or mimic, of the insect molting hormone, 20-hydroxyecdysone (20E). Methoxyfenozide exhibits high insecticidal efficacy against a wide range of important caterpillar pests, including many species of lepidopteran insects.including navel orangeworm, peach twig borer, leafrollers, loopers, armyworms and citrus leafminers. |
| FRCD ID | F05104 |
| CAS Number | 161050-58-4 |
| PubChem CID | 105010 |
| Formula | C22H28N2O3 |
| IUPAC Name | N'-tert-butyl-N'-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide |
| InChI Key | QCAWEPFNJXQPAN-UHFFFAOYSA-N |
| InChI | InChI=1S/C22H28N2O3/c1-14-11-15(2)13-17(12-14)21(26)24(22(4,5)6)23-20(25)18-9-8-10-19(27-7)16(18)3/h8-13H,1-7H3,(H,23,25) |
| Canonical SMILES | CC1=CC(=CC(=C1)C(=O)N(C(C)(C)C)NC(=O)C2=C(C(=CC=C2)OC)C)C |
| Isomeric SMILES | CC1=CC(=CC(=C1)C(=O)N(C(C)(C)C)NC(=O)C2=C(C(=CC=C2)OC)C)C |
| Synonyms |
161050-58-4
N'-(tert-Butyl )-N'-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide
Methoxyfenozide
Methoxyphenozide
Intrepid
N'-tert-Butyl-N'-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide
N'-(tert-butyl)-N'-(3,5-dimethylbenzoyl)-3-methoxy-2-methylbenzohydrazide
RH 2485
3-Methoxy-2-methylbenzoic acid 2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl)hydrazide
UNII-62A22651ZX
|
| 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 - Phenoxy compound - Anisole - Benzoyl - M-xylene - Xylene - Phenol ether - Methoxybenzene - Alkyl aryl ether - Toluene - Carboxylic acid derivative - Ether - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Organic oxide - Organopnictogen compound - Organooxygen compound - Hydrocarbon derivative - 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 | 368.477 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 4 |
| Complexity | 518 |
| Monoisotopic Mass | 368.21 |
| Exact Mass | 368.21 |
| XLogP | 4.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 27 |
| 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+ | 0.9143 |
| Human Intestinal Absorption | HIA+ | 0.9943 |
| Caco-2 Permeability | Caco2+ | 0.8199 |
| P-glycoprotein Substrate | Non-substrate | 0.6886 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.5215 |
| Non-inhibitor | 0.8901 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9016 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.9225 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7137 |
| CYP450 2D6 Substrate | Non-substrate | 0.7899 |
| CYP450 3A4 Substrate | Substrate | 0.6656 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5526 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.6680 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9363 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5926 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.6478 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5725 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9902 |
| Non-inhibitor | 0.8592 | |
| AMES Toxicity | Non AMES toxic | 0.7779 |
| Carcinogens | Non-carcinogens | 0.6064 |
| Fish Toxicity | High FHMT | 0.9793 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7654 |
| Honey Bee Toxicity | Low HBT | 0.7271 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7760 |
| Carcinogenicity (Three-class) | Non-required | 0.5043 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.7451 | LogS |
| Caco-2 Permeability | 1.3666 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8989 | LD50, mol/kg |
| Fish Toxicity | 0.1470 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4807 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe... | 0632010 | European Union | 0.05* | 21/01/2016 | |
| Blackberries | 0153010 | European Union | 0.01* | 21/01/2016 | |
| (c) cane fruits | 0153000 | European Union | 0.01* | 21/01/2016 | |
| Citrus fruits | 0110000 | European Union | 2 | 21/01/2016 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 2 | 21/01/2016 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 2 | 21/01/2016 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 2 | 21/01/2016 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 2 | 21/01/2016 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 2 | 21/01/2016 | |
| Others (2) | 0110990 | European Union | 2 | 21/01/2016 | |
| Tree nuts | 0120000 | European Union | 0.1 | 21/01/2016 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.1 | 21/01/2016 | |
| Brazil nuts | 0120020 | European Union | 0.1 | 21/01/2016 | |
| Cashew nuts | 0120030 | European Union | 0.1 | 21/01/2016 | |
| Chestnuts | 0120040 | European Union | 0.1 | 21/01/2016 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.1 | 21/01/2016 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.1 | 21/01/2016 | |
| Macadamias | 0120070 | European Union | 0.1 | 21/01/2016 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.1 | 21/01/2016 | |
| Pistachios | 0120100 | European Union | 0.1 | 21/01/2016 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Simultaneous determination of neonicotinoid insecticides and insect growthregulators residues in honey using LC-MS/MS with anion exchanger-disposablepipette extraction. | J Chromatogr A | 2018 Jul 6 | 29735281 |
| Direct residue analysis of systemic insecticides and some of their relevantmetabolites in wines by liquid chromatography - mass spectrometry. | J Chromatogr A | 2017 Jul 14 | 28549715 |
| Survival and growth of foodborne pathogens in pesticide solutions routinely used in leafy green vegetables and tomato production. | J Sci Food Agric | 2014 Nov | 24615509 |
| Xenobiotic effects on intestinal stem cell proliferation in adult honey bee (Apismellifera L) workers. | PLoS One | 2014 Mar 7 | 24608542 |
| The impact of insecticides applied in apple orchards on the predatory miteKampimodromus aberrans (Acari: Phytoseiidae). | Exp Appl Acarol | 2014 Mar | 24114337 |
| The effect of insecticides on the non-target predatory mite Kampimodromusaberrans: laboratory studies. | Chemosphere | 2013 Oct | 23856464 |
| Development of a rapid resistance monitoring bioassay for codling moth larvae. | Pest Manag Sci | 2012 Jun | 22262512 |
| Life stage toxicity and residual activity of insecticides to codling moth andoriental fruit moth (Lepidoptera: Tortricidae). | J Econ Entomol | 2011 Dec | 22299357 |
| Effects of six selected orchard insecticides on Neoseiulus fallacis (Acari: Phytoseiidae) in the laboratory. | Pest Manag Sci | 2010 Nov | 20715016 |
| [Determination of benzoylurea and bishydrazide pesticide residues in vegetablesby ultra performance liquid chromatography-tandem mass spectrometry with matrixsolid phase dispersion]. | Se Pu | 2010 Apr | 20712114 |
| Influence of Lobesia botrana field control on black aspergilli rot and ochratoxin A contamination in grapes. | J Food Prot | 2009 Apr | 19435246 |
| Influence of mixtures of kaolin particle film and synthetic insecticides on mortality of larval obliquebanded leafrollers (Lepidoptera: Tortricidae) from resistant and susceptible populations. | J Econ Entomol | 2007 Dec | 18232400 |
| Novel life stage targets against plum curculio, Conotrachelus nenuphar (Herbst), in apple integrated pest management. | Pest Manag Sci | 2007 Aug | 17575566 |
| Assessment of sublethal effects of methoxyfenozide on oriental fruit Moth(Lepidoptera: Tortricidae). | J Econ Entomol | 2005 Jun | 16022304 |
| Development, oviposition, and mortality of Neoseiulus fallacis (Acari: Phytoseiidae) in response to reduced-risk insecticides. | J Econ Entomol | 2005 Dec | 16539140 |
| Stage-specific control of grape berry moth, Endopiza viteana (Clemens)(Lepidoptera: Tortricidae), by selective and broad-spectrum insecticides. | J Econ Entomol | 2005 Apr | 15889733 |
| Analysis of methoxyfenozide residues in fruits, vegetables, and mint by liquidchromatography-tandem mass spectrometry (LC-MS/MS). | J Agric Food Chem | 2004 Feb 25 | 14969514 |
| Oriental fruit moth (Lepidoptera: Tortricidae) phenology and management withmethoxyfenozide in North Carolina apples. | J Econ Entomol | 2004 Aug | 15384348 |
| Toxicity and residual activity of methoxyfenozide and tebufenozide to codlingmoth (Lepidoptera: Tortricidae) and oriental fruit moth (Lepidoptera:Tortricidae). | J Econ Entomol | 2004 Aug | 15384347 |
| Resistance and cross-resistance to four insecticides in populations ofobliquebanded leafroller (Lepidoptera: Tortricidae). | J Econ Entomol | 2002 Aug | 12216826 |
Targets
- 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. 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:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 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 hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B/WSTF which mediates the interaction with acetylated histones, an essential step for VDR-promoter association. Plays a central role in calcium homeostasis.
- Gene Name:
- VDR
- Uniprot ID:
- P11473
- Molecular Weight:
- 48288.64 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:
- Iron ion binding
- Specific Function:
- Catalyzes the conversion of 25-hydroxyvitamin D3 (25(OH)D) to 1-alpha,25-dihydroxyvitamin D3 (1,25(OH)2D) plays an important role in normal bone growth, calcium metabolism, and tissue differentiation.
- Gene Name:
- CYP27B1
- Uniprot ID:
- O15528
- Molecular Weight:
- 56503.475 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:
- Receptor binding
- Specific Function:
- Chemotactic for monocytes and T-lymphocytes. Binds to CXCR3.
- Gene Name:
- CXCL10
- Uniprot ID:
- P02778
- Molecular Weight:
- 10880.915 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:
- 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 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:
- 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 ]