Novaluron
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Basic Info
| Common Name | Novaluron(F05428) |
| 2D Structure | |
| Description | Novaluron is a chemical with pesticide properties, belonging to the class of new insect growth regulators used to control a range of pests including Lepidoptera, Coleoptera, and Diptera. It is a chitin synthesis inhibitor, with stomach action and some contact activity. In the United States, the compound has been used on food crops, including apples, potatoes, brassicas, ornamentals and cotton. The US Environmental Protection Agency and the Canadian Pest Management Regulatory Agency consider novaluron to pose low risk to the environment and non-target organisms, and value it an important option for integrated pest management that should decrease reliance on organophosphorus, carbamate and pyrethroid insecticides. |
| FRCD ID | F05428 |
| CAS Number | 116714-46-6 |
| PubChem CID | 93541 |
| Formula | C17H9ClF8N2O4 |
| IUPAC Name | N-[[3-chloro-4-[1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy]phenyl]carbamoyl]-2,6-difluorobenzamide |
| InChI Key | NJPPVKZQTLUDBO-UHFFFAOYSA-N |
| InChI | InChI=1S/C17H9ClF8N2O4/c18-8-6-7(4-5-11(8)31-16(22,23)14(21)32-17(24,25)26)27-15(30)28-13(29)12-9(19)2-1-3-10(12)20/h1-6,14H,(H2,27,28,29,30) |
| Canonical SMILES | C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=CC(=C(C=C2)OC(C(OC(F)(F)F)F)(F)F)Cl)F |
| Isomeric SMILES | C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=CC(=C(C=C2)OC(C(OC(F)(F)F)F)(F)F)Cl)F |
| Synonyms |
116714-46-6
Benzamide, N-3-chloro-4-(1,1,2-trifluoro)-2-(trifluoromethoxy)ethoxyphenyl-amino-carbonyl-2,6-difluoro-
Novaluron
Rimon
Novaluron [ISO]
HSDB 7004
CHEBI:39385
NJPPVKZQTLUDBO-UHFFFAOYSA-N
1-[3-Chloro-4-(1,1,2-trifluoro-2-trifluoromethoxyethoxy)phenyl]-3-(2,6-difluorobenzoyl)urea
N-({3-chloro-4-[1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy]phenyl}carbamoyl)-2,6-difluorobenzamide
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenol ethers |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenol ethers |
| Alternative Parents |
|
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Phenoxy compound - Phenol ether - Chlorobenzene - Fluorobenzene - Halobenzene - Aryl chloride - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - Trihalomethane - Carboximidic acid derivative - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Alkyl fluoride - Organochloride - Organohalogen compound - Organofluoride - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Halomethane - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Alkyl halide - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 492.706 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 6 |
| Complexity | 661 |
| Monoisotopic Mass | 492.012 |
| Exact Mass | 492.012 |
| XLogP | 5.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 32 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| 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+ | 0.9531 |
| Human Intestinal Absorption | HIA+ | 0.9391 |
| Caco-2 Permeability | Caco2- | 0.5457 |
| P-glycoprotein Substrate | Non-substrate | 0.7123 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7248 |
| Non-inhibitor | 0.8976 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9193 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7670 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6989 |
| CYP450 2D6 Substrate | Non-substrate | 0.8277 |
| CYP450 3A4 Substrate | Non-substrate | 0.5815 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6009 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.5444 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8273 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.6578 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9136 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5985 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9839 |
| Non-inhibitor | 0.8398 | |
| AMES Toxicity | Non AMES toxic | 0.8071 |
| Carcinogens | Non-carcinogens | 0.7092 |
| Fish Toxicity | High FHMT | 0.9880 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9990 |
| Honey Bee Toxicity | Low HBT | 0.8544 |
| Biodegradation | Not ready biodegradable | 0.9888 |
| Acute Oral Toxicity | III | 0.7236 |
| Carcinogenicity (Three-class) | Non-required | 0.5334 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -5.2429 | LogS |
| Caco-2 Permeability | 0.8203 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1126 | LD50, mol/kg |
| Fish Toxicity | 0.4565 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.2417 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Quinces (Chinese quinces, Japanese quinces,) | 0130030 | European Union | 0.01* | 14/06/2012 | |
| Cherries (sweet) (Black cherries, Capulins, Chokecherries, Cornelian cherries/European corniols, Nanking cherries, Sour cherries/morello cherries,) | 0140020 | European Union | 7 | 14/06/2012 | |
| Avocados (Avocados for oil production,) | 0163010 | European Union | 0.01* | 14/06/2012 | |
| Others (2) | 0233990 | European Union | 0.2 | 14/06/2012 | |
| (e) other fruiting vegetables | 0239000 | European Union | 0.01* | 14/06/2012 | |
| Tarragon (Aztec sweet herb, Epazote/Mexican tea/wormseed, Hyssop, Lemongrass, Mexican oregano, Nettle, Other species of the genus Urtica, not elsewhere mentioned, Russian tarragon, Stevia,) | 0256100 | European Union | 0.01* | 14/06/2012 | |
| Beans (with pods) (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap beans, ... | 0260010 | European Union | 0.7 | 14/06/2012 | |
| Olives for oil production | 0402010 | European Union | 0.01* | 14/06/2012 | |
| Oil palms kernels (Argan nuts, Babassu palm nuts, Jojoba nuts, Shea nuts,) | 0402020 | European Union | 0.01* | 14/06/2012 | |
| Black caraway/black cumin (Nigella,) | 0810020 | European Union | 0.01* | 14/06/2012 | |
| Nutmeg (Annatto, Candlenut, Wattleseeds, Calabash nutmeg,) | 0810090 | European Union | 0.01* | 14/06/2012 | |
| Kidney | 1016040 | European Union | 0.1 | 14/06/2012 | |
| Others (2) (Bactrian camel, Dromedary, Elk/moose, Reindeer, Other milk producer animals,) | 1020990 | European Union | 0.4 | 14/06/2012 | |
| Mayhaws | Canada | 2mg/kg | |||
| Citrus fruits | 0110000 | European Union | 0.01* | 14/06/2012 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 14/06/2012 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 14/06/2012 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 14/06/2012 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 14/06/2012 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.01* | 14/06/2012 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Transovarial Effect of Novaluron on Tribolium castaneum (Coleoptera:Tenebrionidae) After Termination of Direct Contact. | J Insect Sci | 2015 Sep 10 | 26363061 |
| A novel bioassay to evaluate the potential of Beauveria bassiana strain NI8 and the insect growth regulator novaluron against Lygus lineolaris on a non-autoclaved solid artificial diet. | J Insect Sci | 2014 | 25368059 |
| Evaluation of three feed-through insecticides using two rodent and two sand flyspecies as models. | J Am Mosq Control Assoc | 2012 Sep | 23833909 |
| Laboratory-based toxicological assessments of new insecticides on mortality and fecundity of Neoseiulus fallacis (Acari: Phytoseiidae). | J Econ Entomol | 2012 Jun | 22812123 |
| Development of a rapid resistance monitoring bioassay for codling moth larvae. | Pest Manag Sci | 2012 Jun | 22262512 |
| Efficacy of commercial baits and new active ingredients against firebrats andsilverfish (Zygentoma: Lepismatidae). | J Econ Entomol | 2012 Aug | 22928320 |
| Residual activity of methoprene and novaluron as surface treatments to manage theflour beetles, Tribolium castaneum and Tribolium confusum. | J Insect Sci | 2012 | 23421852 |
| A laboratory assessment of the toxic attributes of six 'reduced risk insecticides' on Galendromus occidentalis (Acari: Phytoseiidae). | Chemosphere | 2011 Jun | 21458842 |
| Life stage toxicity and residual activity of insecticides to codling moth andoriental fruit moth (Lepidoptera: Tortricidae). | J Econ Entomol | 2011 Dec | 22299357 |
| 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 |
| Synthesis and insecticidal activity of heptafluoroisopropyl-containingbenzoylphenylurea structures. | J Agric Food Chem | 2010 Mar 10 | 20014763 |
| Laboratory evaluation of novaluron as a rodent feed-through insecticide againstsand fly larvae (Diptera: Psychodidae). | J Med Entomol | 2010 Mar | 20380301 |
| Evaluation of novaluron as a feed-through insecticide for control of immaturesand flies (Diptera: Psychodidae). | J Med Entomol | 2007 Jul | 17695030 |
| Topical, residual and ovicidal contact toxicity of three reduced-riskinsecticides against the European corn borer, Ostrinia nubilalis (Lepidoptera:Crambidae), on potato. | Pest Manag Sci | 2007 Dec | 17890653 |
| Novel life stage targets against plum curculio, Conotrachelus nenuphar (Herbst), in apple integrated pest management. | Pest Manag Sci | 2007 Aug | 17575566 |
Targets
- 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 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:
- 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:
- Transmembrane signaling receptor activity
- Specific Function:
- Cell-surface glycoprotein having a role in immunoadhesion. Mediates in the adhesion of blood neutrophils in cytokine-activated endothelium through interaction with PSGL1/SELPLG. May have a role in capillary morphogenesis.
- Gene Name:
- SELE
- Uniprot ID:
- P16581
- Molecular Weight:
- 66654.575 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:
- Thrombomodulin is a specific endothelial cell receptor that forms a 1:1 stoichiometric complex with thrombin. This complex is responsible for the conversion of protein C to the activated protein C (protein Ca). Once evolved, protein Ca scissions the activated cofactors of the coagulation mechanism, factor Va and factor VIIIa, and thereby reduces the amount of thrombin generated.
- Gene Name:
- THBD
- Uniprot ID:
- P07204
- Molecular Weight:
- 60328.72 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 ]