Flumioxazin
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Basic Info
| Common Name | Flumioxazin(F05076) |
| 2D Structure | |
| Description | Flumioxazin is a broad-spectrum contact herbicide. It works by interfering with the plants’ production of chlorophyll. Treated plants will respond quickly to treatment and rapidly decompose. Flumioxazin is an N-phenylphthalimide herbicide. The mode of action in this family of herbicides is believed to be inhibition of protoporphyrinogen oxidase, an enzyme important in the synthesis of chlorophyll. Mechanistic study findings suggest that porphyrins accumulate in susceptible plants causing photosensitization, which leads to membrane lipid peroxidation. The peroxidation of membrane lipids leads to irreversible damage of membrane function and structure in susceptible plants. Treatment of soil with flumioxazin will cause susceptible emerging plants to turn necrotic and die shortly after exposure to sunlight. Flumioxazin is used on soybeans, peanuts, orchard fruits and other crops. Flumioxazin is also used to controls invasive Eurasian watermilfoil (Myriophyllum spicatum) and curlyleaf pondweed (Potamogeton crispus). Flumioxazin has been used as an agricultural chemical since 2001, and was conditionally registered for aquatic use in 2010. |
| FRCD ID | F05076 |
| CAS Number | 103361-09-7 |
| PubChem CID | 92425 |
| Formula | C19H15FN2O4 |
| IUPAC Name | 2-(7-fluoro-3-oxo-4-prop-2-ynyl-1,4-benzoxazin-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione |
| InChI Key | FOUWCSDKDDHKQP-UHFFFAOYSA-N |
| InChI | InChI=1S/C19H15FN2O4/c1-2-7-21-15-9-14(13(20)8-16(15)26-10-17(21)23)22-18(24)11-5-3-4-6-12(11)19(22)25/h1,8-9H,3-7,10H2 |
| Canonical SMILES | C#CCN1C(=O)COC2=CC(=C(C=C21)N3C(=O)C4=C(C3=O)CCCC4)F |
| Isomeric SMILES | C#CCN1C(=O)COC2=CC(=C(C=C21)N3C(=O)C4=C(C3=O)CCCC4)F |
| Synonyms |
HSDB 7012
Flumioxazin
103361-09-7
Sumisoya
Flumioxazine
Flumioxazin [ISO]
S 53482
S-53482
UNII-L0PX7OGI22
V 53482
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Benzoxazines |
| Subclass | Benzoxazinones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzoxazinones |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Benzoxazinone - Isoindolone - Benzomorpholine - Isoindole or derivatives - Isoindole - Maleimide - Alkyl aryl ether - Benzenoid - Oxazinane - Carboxylic acid imide, n-substituted - Aryl fluoride - Aryl halide - Carboxylic acid imide - Dicarboximide - Tertiary carboxylic acid amide - Pyrroline - Carboxamide group - Lactam - Acetylide - Carboxylic acid derivative - Oxacycle - Azacycle - Ether - Organopnictogen compound - Organic oxygen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 354.337 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Complexity | 724 |
| Monoisotopic Mass | 354.102 |
| Exact Mass | 354.102 |
| XLogP | 1.8 |
| 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 |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Cultivated fungi (Common mushrooms/button mushrooms/champignons mushrooms, Corn smuts/ Mexican truffles, Enokitake/winter mushrooms, Fusarium venenatum, Horse mushrooms, Jew's ears/hirneola, Nameko... | 0280010 | European Union | 0.02* | 13/05/2015 | |
| TEAS, COFFEE, HERBAL INFUSIONS, COCOA AND CAROBS | 0600000 | European Union | 0.1* | 13/05/2015 | |
| Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei... | 0631030 | European Union | 0.1* | 13/05/2015 | |
| Seed spices | 0810000 | European Union | 0.1* | 13/05/2015 | |
| Cocoa beans (Kola nuts/Cola nuts, Cupuaçu,) | 0640000 | European Union | 0.1* | 13/05/2015 | |
| Celeries | 0270030 | European Union | 0.02* | 13/05/2015 | |
| Florence fennels | 0270040 | European Union | 0.02* | 13/05/2015 | |
| Globe artichokes (Banana flowers,) | 0270050 | European Union | 0.02* | 13/05/2015 | |
| Leeks (Kurrat/Egyptian leek,) | 0270060 | European Union | 0.02* | 13/05/2015 | |
| Rhubarbs | 0270070 | European Union | 0.02* | 13/05/2015 | |
| Bamboo shoots (European bamboo /Japanese knotweed,) | 0270080 | European Union | 0.02* | 13/05/2015 | |
| Palm hearts | 0270090 | European Union | 0.02* | 13/05/2015 | |
| Others (2) | 0270990 | European Union | 0.02* | 13/05/2015 | |
| Fungi, mosses and lichens | 0280000 | European Union | 0.02* | 13/05/2015 | |
| Wild fungi (Ceps/porcino mushrooms, Chanterelles, Hedgehog mushrooms, Horns of plenty/black trumpets, Morels, Périgord black truffles, Piemont white truffles, Saint George's mushrooms, Scotch bonne... | 0280020 | European Union | 0.02* | 13/05/2015 | |
| Mosses and lichens (Icelandic mosses, Other mosses and lichens,) | 0280990 | European Union | 0.02* | 13/05/2015 | |
| Algae and prokaryotes organisms (Carrageen mosses/Irish mosses, Kombu, Spirulina, Spirulina, Other algae, Other procaryotes organisms, Rockweed /knotted kelp,) | 0290000 | European Union | 0.02* | 13/05/2015 | |
| PULSES | 0300000 | European Union | 0.02* | 13/05/2015 | |
| Carobs/Saint John's breads (Jengkols/Luk neangs,) | 0650000 | European Union | 0.1* | 13/05/2015 | |
| HOPS | 0700000 | European Union | 0.1* | 13/05/2015 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Determination of flumioxazin residue in food samples through a sensitivefluorescent sensor based on click chemistry. | Food Chem | 2014 Nov 1 | 24874382 |
| Novel colorimetric molecular switch based on copper(I)-catalyzed azide-alkynecycloaddition reaction and its application for flumioxazin detection. | Analyst | 2013 Jan 21 | 23188065 |
| Synthesis and herbicidal activity of isoindoline-1,3-dione substitutedbenzoxazinone derivatives containing a carboxylic ester group. | J Agric Food Chem | 2009 Oct 28 | 19772294 |
| [Determination of flumioxazin residue in foods using gas chromatography-massspectrometry]. | Se Pu | 2008 May | 18724667 |
| Flumioxazin soil persistence and mineralization in laboratory experiments. | J Agric Food Chem | 2003 Jul 30 | 14705902 |
| Effects of flumioxazin herbicide on carbon nutrition of Vitis vinifera L. | J Agric Food Chem | 2003 Jul 2 | 12822940 |
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:
- This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible for the epoxidation of endogenous cardiac arachidonic acid pools.
- Gene Name:
- CYP2J2
- Uniprot ID:
- P51589
- Molecular Weight:
- 57610.165 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:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TGFA/TGF-alpha, amphiregulin, epigen/EPGN, BTC/betacellulin, epiregulin/EREG and HBEGF/heparin-binding EGF. Ligand binding triggers receptor homo- and/or heterodimerization and autophosphorylation on key cytoplasmic residues. The phosphorylated receptor recruits adapter proteins like GRB2 which in turn activates complex downstream signaling cascades. Activates at least 4 major downstream signaling cascades including the RAS-RAF-MEK-ERK, PI3 kinase-AKT, PLCgamma-PKC and STATs modules. May also activate the NF-kappa-B signaling cascade. Also directly phosphorylates other proteins like RGS16, activating its GTPase activity and probably coupling the EGF receptor signaling to the G protein-coupled receptor signaling. Also phosphorylates MUC1 and increases its interaction with SRC and CTNNB1/beta-catenin.Isoform 2 may act as an antagonist of EGF action.
- Gene Name:
- EGFR
- Uniprot ID:
- P00533
- Molecular Weight:
- 134276.185 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 ]