T3DB: Fluazifop-butyl

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (3)XML

Targets (3)

Record Information

Version

2.0

Creation Date

2013-04-25 07:56:51 UTC

Update Date

2014-12-24 20:26:33 UTC

Accession Number

T3D3840

Identification

Common Name

Fluazifop-butyl

Class

Small Molecule

Description

Fluazifop-butyl is an aryloxyphenoxypropionic herbicide used for postemergence control of annual and perennial grass weeds. This substance is a derivative of fluazifop. Fluazifop-butyl is a different compound than either fluazifop or fluazifop-p-butyl. Both the chemical structures and the toxicities of these compounds are different. Fluazifop-p-butyl formulations can contain some fluazifop-butyl.

Compound Type

Ester
Ether
Herbicide
Organic Compound
Organofluoride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
2-(4-((5-(Trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propanoic acid butyl ester
2-(4-((5-(Trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propanoic acid, butyl ester
2-[4-[[5-(Trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic Acid Butyl Ester
Butyl (RS)-2-(4-((5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propanoate
Butyl 2-(4-((5-(trifluoromethyl)-2-pyridyl)oxy)phenoxy)propionate
Butyl 2-(4-([5-(trifluoromethyl)-2-pyridinyl]oxy)phenoxy)propanoate
Butyl 2-(4-{[5-(trifluoromethyl)-2-pyridinyl]oxy}phenoxy)propanoate
Butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate
Butyl 2-[4-(5-Trifluoromethyl-2-pyridyloxy)phenoxy]propionate
Fluazifop butyl
Fluazifop-p butyl
Fusilade
Halokon
Onecide

Chemical Formula

C₁₉H₂₀F₃NO₄

Average Molecular Mass

383.362 g/mol

Monoisotopic Mass

383.134 g/mol

CAS Registry Number

69806-50-4

IUPAC Name

butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate

Traditional Name

fusilade

SMILES

CCCCOC(=O)C(C)OC1=CC=C(OC2=NC=C(C=C2)C(F)(F)F)C=C1

InChI Identifier

InChI=1S/C19H20F3NO4/c1-3-4-11-25-18(24)13(2)26-15-6-8-16(9-7-15)27-17-10-5-14(12-23-17)19(20,21)22/h5-10,12-13H,3-4,11H2,1-2H3

InChI Key

InChIKey=VAIZTNZGPYBOGF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 2-phenoxypropionic acid esters. These are aromatic compounds hat contain a phenol ether attached to the C2-atom of a phenylpropionic acid ester.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

2-phenoxypropionic acid esters

Direct Parent

2-phenoxypropionic acid esters

Alternative Parents

Substituents

2-phenoxypropionic acid ester
Diaryl ether
Phenoxyacetate
Phenoxy compound
Phenol ether
Alkyl aryl ether
Pyridine
Heteroaromatic compound
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organofluoride
Organohalogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Alkyl halide
Alkyl fluoride
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:5097 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0031 g/L	ALOGPS
logP	4.86	ALOGPS
logP	5.09	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	0.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.65 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	92.11 m³·mol⁻¹	ChemAxon
Polarizability	36.7 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-8091000000-2b8d619eea150a4792b7	2021-09-24	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-0019000000-b0f1c4b0b33e4972089e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0092000000-6d191c1c26944c3f3fd7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-000f-9280000000-b96d1ae098e0c1556793	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-000x-5190000000-828dcde46313614790e1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0006-9460000000-97319d290772f84f9f97	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-0019000000-cee769fc69cac8849bbc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-000x-5190000000-6199bc42e11ccc6fe811	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-00kf-9830000000-96ea29959bce6dbde09f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0093000000-7411ae83cac9706361ac	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0f8c-3090000000-800896d901b728c92d96	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0006-9460000000-0227fc7cd4973029f9d2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-000f-6390000000-e45750265a84c412d7e6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0f76-4190000000-579e1740e231ab7f24cd	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-053r-3029000000-c312c444eab9c43d83aa	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9153000000-d99dadceeec0ca78424b	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9360000000-3f78140c08d4f0d117df	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-053r-3029000000-1b86d11702527cf3de3e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-4159000000-2b1c64be8de56e530025	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-2940000000-ce12649a421bf1c5defc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0019000000-65ae134c482bebb85677	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1095000000-15aa0e98db885c583abe	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-4490000000-df85c6a40d94811590a7	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0109000000-a8525022a6f9821f41e0	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0h90-9565000000-f477edeab4ceeedec9d6	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0w29-1790000000-1a0097aba221d5d58c44	2021-10-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-4391000000-8f8562a82faa5ee3f41a	2014-10-20	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D3840.pdf

General References

Not Available

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Cytochrome P450 2B6

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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.43 uM	CLZD_CYP2B6_48	CellzDirect

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 ]

Target Details

2. Hydroxymethylglutaryl-CoA synthase, mitochondrial

General Function:: Hydroxymethylglutaryl-coa synthase activity
Specific Function:: This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:: HMGCS2
Uniprot ID:: P54868
Molecular Weight:: 56634.915 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	9.02 uM	CLZD_HMGCS2_24	CellzDirect

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 ]

Target Details

3. Nuclear receptor subfamily 1 group I member 2

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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	9.70 uM	NVS_NR_hPXR	Novascreen

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 ]

Fluazifop-butyl (T3D3840)

Structure for T3D3840: Fluazifop-butyl

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References