Flumetsulam
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Basic Info
| Common Name | Flumetsulam(F05074) |
| 2D Structure | |
| Description | Flumetsulam is a sulfonanilide herbicide that is used for post-emergence control for undersown wheat and certain legume crops and pastures. |
| FRCD ID | F05074 |
| CAS Number | 98967-40-9 |
| PubChem CID | 91759 |
| Formula | C12H9F2N5O2S |
| IUPAC Name | N-(2,6-difluorophenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide |
| InChI Key | RXCPQSJAVKGONC-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H9F2N5O2S/c1-7-5-6-19-11(15-7)16-12(17-19)22(20,21)18-10-8(13)3-2-4-9(10)14/h2-6,18H,1H3 |
| Canonical SMILES | CC1=NC2=NC(=NN2C=C1)S(=O)(=O)NC3=C(C=CC=C3F)F |
| Isomeric SMILES | CC1=NC2=NC(=NN2C=C1)S(=O)(=O)NC3=C(C=CC=C3F)F |
| Synonyms |
Flumetsulam
98967-40-9
Broadstrike
N-(2,6-difluorophenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide
UNII-X89F0S6LW8
XRD 498
DE 498
EPA Pesticide Chemical Code 129016
X89F0S6LW8
CHEBI:82011
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Triazolopyrimidines |
| Subclass | 1,2,4-triazolopyrimidine-2-sulfonamides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | 1,2,4-triazolopyrimidine-2-sulfonanilides |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | 1,2,4-triazolopyrimidine-2-sulfonanilide - Sulfanilide - Halobenzene - Fluorobenzene - Pyrimidine - Aryl fluoride - Organosulfonic acid amide - Benzenoid - Aryl halide - Monocyclic benzene moiety - 1,2,4-triazole - Triazole - Aminosulfonyl compound - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Heteroaromatic compound - Azole - Sulfonyl - Azacycle - Organonitrogen compound - Organofluoride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organosulfur compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as 1,2,4-triazolopyrimidine-2-sulfonanilides. These are polycyclic aromatic compounds containing a 1,2,4-triazolo[1,5-a]pyrimidine ring system, which is substituted with a sulfonanilide at the 2-position. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 325.294 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 3 |
| Complexity | 492 |
| Monoisotopic Mass | 325.045 |
| Exact Mass | 325.045 |
| XLogP | 1.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| 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+ | 0.5981 |
| Human Intestinal Absorption | HIA+ | 0.9942 |
| Caco-2 Permeability | Caco2+ | 0.5342 |
| P-glycoprotein Substrate | Non-substrate | 0.8418 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6787 |
| Non-inhibitor | 0.7668 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8186 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4768 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7050 |
| CYP450 2D6 Substrate | Non-substrate | 0.7539 |
| CYP450 3A4 Substrate | Non-substrate | 0.5859 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6292 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6031 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8902 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.6023 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.5858 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6111 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8065 |
| Non-inhibitor | 0.8266 | |
| AMES Toxicity | Non AMES toxic | 0.7622 |
| Carcinogens | Non-carcinogens | 0.8031 |
| Fish Toxicity | High FHMT | 0.9824 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8731 |
| Honey Bee Toxicity | Low HBT | 0.8836 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7716 |
| Carcinogenicity (Three-class) | Non-required | 0.6383 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.7345 | LogS |
| Caco-2 Permeability | 1.1232 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8448 | LD50, mol/kg |
| Fish Toxicity | 1.6023 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6618 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Other Spices | Japan | 0.1ppm | |||
| Other Legumes/Pulses | Japan | 0.05ppm | |||
| Pig,Liver | Japan | 0.2ppm | |||
| Other Poultry,Eggs | Japan | 0.1ppm | |||
| Chicken,Eggs | Japan | 0.1ppm | |||
| Other Poultry Animals,Edible Offal | Japan | 0.1ppm | |||
| Chicken,Edible Offal | Japan | 0.1ppm | |||
| Other Poultry Animals,Kidney | Japan | 0.1ppm | |||
| Chicken,Kidney | Japan | 0.1ppm | |||
| Other Poultry Animals,Liver | Japan | 0.1ppm | |||
| Chicken,Liver | Japan | 0.1ppm | |||
| Other Poultry Animals,Fat | Japan | 0.1ppm | |||
| Chicken,Fat | Japan | 0.1ppm | |||
| Other Poultry Animals,Muscle | Japan | 0.1ppm | |||
| Chicken,Muscle | Japan | 0.1ppm | |||
| Milk | Japan | 0.1ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 0.2ppm | |||
| Pig,Edible Offal | Japan | 0.2ppm | |||
| Cattle,Edible Offal | Japan | 0.2ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 0.2ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Design, Synthesis, and Herbicidal Activity of Pyrimidine-Biphenyl Hybrids asNovel Acetohydroxyacid Synthase Inhibitors. | J Agric Food Chem | 2018 Apr 18 | 29618205 |
| Dissipation and residues of flumetsulam in wheat and soil. | Bull Environ Contam Toxicol | 2012 Jun | 22460803 |
| Rapid residue analysis of four triazolopyrimidine herbicides in soil, water, and wheat by ultra-performance liquid chromatography coupled to tandem massspectrometry. | Anal Bioanal Chem | 2011 Mar | 21221546 |
| Development of an improved liquid phase microextraction technique and itsapplication in the analysis of flumetsulam and its two analogous herbicides insoil. | J Agric Food Chem | 2007 Nov 14 | 17953444 |
| Rapid analysis of triazolopyrimidine sulfoanilide herbicides in waters and soils by high-performance liquid chromatography with UV detection using a C18monolithic column. | J Sep Sci | 2007 Jan | 17313135 |
| Liquid chromatographic determination of flumetsulam in soybeans. | J AOAC Int | 2005 Sep-Oct | 16385997 |
| Analysis of pesticides in soy milk combining solid-phase extraction and capillaryelectrophoresis-mass spectrometry. | J Sep Sci | 2005 Jun | 16013821 |
| Analysis of triazolopyrimidine herbicides in soils using field-enhanced sampleinjection-coelectroosmotic capillary electrophoresis combined with solid-phaseextraction. | J Chromatogr A | 2005 Dec 30 | 16212970 |
Targets
- 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 ]