Page last updated: 2024-12-06

fluazifop-butyl

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Fluazifop-butyl is a selective herbicide that belongs to the aryloxyphenoxypropionate family. It is primarily used to control annual and perennial grasses in broadleaf crops. Fluazifop-butyl is a synthetic compound that inhibits the biosynthesis of fatty acids in plants, particularly in grasses. It is absorbed by the leaves and translocated to the growing points, where it disrupts the synthesis of fatty acids essential for cell growth and division. Fluazifop-butyl is highly effective in controlling a wide range of grass weeds, including wild oats, barnyardgrass, and quackgrass. It is commonly used in various crops such as soybeans, cotton, sugar beets, and alfalfa. Its effectiveness is attributed to its selective action, which targets grasses without causing significant damage to broadleaf crops. The synthesis of fluazifop-butyl involves a multi-step process that starts with the reaction of a phenoxypropionic acid derivative with a substituted aniline. This is followed by a series of reactions, including alkylation and esterification, to obtain the final product. Extensive research on fluazifop-butyl has focused on its selectivity, efficacy, environmental fate, and potential for resistance development. These studies aim to understand its mode of action, optimize its use, and ensure its sustainable application in agriculture.'

fluazifop-butyl: RN given for cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

fluazifop-butyl : A racemate that is the butyl ester of fluazifop. It is used as a post-emergence herbicide for the control grass weeds in various broad-leaved crops. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate : A carboxylic ester resulting from the formal condensation of the carboxy group 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid with the hydroxy group of butan-1-ol. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID50897
CHEMBL ID449397
CHEBI ID132963
CHEBI ID5097
SCHEMBL ID54222
MeSH IDM0144348

Synonyms (78)

Synonym
AC-19981
butyl 2-(4-(5-trifluoromethyl-2-pyridinyloxy)phenoxy)propanoate
propanoic acid, 2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]-, butyl ester
(+-)-butyl-2-(4-(((5-trifluoro-methyl)-2-pyridinyl)oxy)phenoxy)propanoate
fusilade 4e
propanoic acid, 2-(4-((5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)-, butyl ester
caswell no. 460c
fluazifop-butyl [iso]
propionic acid, 2-(p-((5-(trifluoromethyl)-2-pyridyl)oxy)phenoxy)-, butyl ester
einecs 274-125-6
onecide
epa pesticide chemical code 122805
tf 1169
butyl (rs)-2-(4-((5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propanoate
2-(4-((5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propanoic acid, butyl ester
hache uno super
fusilade
onecide ec
pp 009
butyl 2-(4-((5-(trifluoromethyl)-2-pyridyl)oxy)phenoxy)propionate
ts-7236
2-(4-((5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propanoic acid butyl ester
hsdb 6644
ih 773b
halokon
69806-50-4
fluazifop butyl
fluazifop-butyl
butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate
NCGC00164281-02
CHEBI:132963
chebi:5097
CHEMBL449397
butyl 2-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoate
NCGC00164281-03
fluazifop-butyl:butyl 2-[4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy]propionate
unii-12o1z35lqa
12o1z35lqa ,
NCGC00254986-01
cas-69806-50-4
tox21_301085
dtxcid1014612
dtxsid3034612 ,
86334-14-7
propanoic acid, 2-(4-((5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)-,butyl ester
AKOS015963166
FT-0630864
FT-0630791
fluazifop-butyl [mi]
fluazifop-butyl, (+/-)-
(+/-)-fluazifop-butyl
pp-009
butyl 2-(4-(5-trifluoromethyl-2-pyridyloxy)phenoxy)propionate
fluazifop-butyl [hsdb]
butyl (rs)-2-(4-((5-(trifluoromethyl)-2- pyridinyl)oxy)phenoxy)propanoate
fluazifop butyl ester
propanoic acid, 2-(4-((5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)-, butyl ester, (+/-)-
2-(4-((5-(trifluoromethyl)-2- pyridinyl)oxy)phenoxy)propanoic acid, butyl ester
tf-1169
(+)-fluazifop-butyl
SCHEMBL54222
butyl 2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionate
n-butyl 2-[4-(5-trifluoromethylpyridin-2-yloxy)phenoxy]propionate
n-butyl 2-[4-(5-trifluoromethylpyrid-2-yloxy)-phenoxy]propionate
W-104585
butyl 2-(4-{[5-(trifluoromethyl)-2-pyridinyl]oxy}phenoxy)propanoate
fluazifop, butyl ester
2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoic acid butyl ester
fusilade w
butyl 2-(4-([5-(trifluoromethyl)-2-pyridinyl]oxy)phenoxy)propanoate #
butyl 2-[4-[[5-(trifluoromethyl)-2-pyridyl]oxy]phenoxy]propanoate
butyl 2-[4-[[5-(trifluoromethyl)-2-pyridyl]oxy]phenoxy]propionate
fluazifop-butyl, pestanal(r), analytical standard
fluazifop-butyl 100 microg/ml in acetonitrile
butyl 2-(4-(5-(trifluoromethyl)pyridin-2-yloxy)phenoxy)propanoate
Q27891163
Z1245537587
EN300-86165

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Urinary excretion rate of the principal metabolite fluazifop, following dosing with the 5% formulation, was described by a two-compartment pharmacokinetic model; the average elimination half-lives of initial and terminal phases were 18 h and approximately 70 h, respectively."( Pharmacokinetics of fluazifop-butyl in human volunteers. II: Dermal dosing.
Auton, TR; Batten, PL; Leeser, JE; Ramsey, JD; Woollen, BH, 1992
)
0.61
" Pharmacokinetic parameters derived from an oral dosing study are combined in a mathematical model with in vitro measurements of dermal absorption of fluazifop-butyl."( Modelling dermal pharmacokinetics using in vitro data. Part II. Fluazifop-butyl in man.
Auton, TR; Ramsey, JD; Woollen, BH, 1993
)
0.72

Bioavailability

Fluazifop-butyl is only slowly and poorly absorbed through human skin. The average rate of absorption (x10(-2) micrograms/hr-1 +/- SE) was not greatly influenced by the dosing vehicle.

ExcerptReferenceRelevance
" It is concluded that fluazifop-butyl is only slowly and poorly absorbed through human skin and has a low potential to accumulate in man."( Pharmacokinetics of fluazifop-butyl in human volunteers. II: Dermal dosing.
Auton, TR; Batten, PL; Leeser, JE; Ramsey, JD; Woollen, BH, 1992
)
0.92

Dosage Studied

The predictive accuracy of in vitro measurements in estimating dermal absorption has been evaluated in rat and human skin using fluazifop-butyl.

ExcerptRelevanceReference
" Urinary excretion rate of the principal metabolite fluazifop, following dosing with the 5% formulation, was described by a two-compartment pharmacokinetic model; the average elimination half-lives of initial and terminal phases were 18 h and approximately 70 h, respectively."( Pharmacokinetics of fluazifop-butyl in human volunteers. II: Dermal dosing.
Auton, TR; Batten, PL; Leeser, JE; Ramsey, JD; Woollen, BH, 1992
)
0.61
"One important factor which may influence the extent and rate of percutaneous absorption is the dosing vehicle."( Effect of dosing vehicle on the dermal absorption of fluazifop-butyl and fomesafen in rats in vivo.
Hilton, J; Rawlings, JM; Trebilcock, KL; Wilks, MF; Woollen, BH, 1994
)
0.54
" dosing studies to predict plasma concentrations and urinary excretion profiles following dermal dosing."( Modelling dermal pharmacokinetics using in vitro data. Part I. Fluazifop-butyl in the rat.
Auton, TR; Ramsey, JD; Woollen, BH, 1993
)
0.53
"In a previous paper it was demonstrated that dermal absorption of the herbicide fluazifop-butyl in the rat could be modelled by combining a knowledge of the pharmacokinetics following intravenous and oral dosing with in vitro measurements of dermal absorption."( Modelling dermal pharmacokinetics using in vitro data. Part II. Fluazifop-butyl in man.
Auton, TR; Ramsey, JD; Woollen, BH, 1993
)
0.75
" Subsequent comparisons of the dose-response characteristics of the original and low dose-selected VLR1 lines demonstrated increased tolerance of diclofop-methyl in the selected line."( Recurrent selection with reduced herbicide rates results in the rapid evolution of herbicide resistance in Lolium rigidum.
Neve, P; Powles, S, 2005
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
carboxylic esterAn ester of a carboxylic acid, R(1)C(=O)OR(2), where R(1) = H or organyl and R(2) = organyl.
organofluorine compoundAn organofluorine compound is a compound containing at least one carbon-fluorine bond.
pyridinesAny organonitrogen heterocyclic compound based on a pyridine skeleton and its substituted derivatives.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AR proteinHomo sapiens (human)Potency2.10490.000221.22318,912.5098AID743063
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency68.58960.001022.650876.6163AID1224838
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency0.38900.000214.376460.0339AID720692
vitamin D (1,25- dihydroxyvitamin D3) receptorHomo sapiens (human)Potency19.49380.023723.228263.5986AID743222
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency6.11310.001723.839378.1014AID743083
thyroid stimulating hormone receptorHomo sapiens (human)Potency32.05420.001628.015177.1139AID1224843; AID1224895; AID1259395
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (34)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (5.88)18.7374
1990's18 (52.94)18.2507
2000's2 (5.88)29.6817
2010's12 (35.29)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 39.30

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index39.30 (24.57)
Research Supply Index3.61 (2.92)
Research Growth Index5.75 (4.65)
Search Engine Demand Index99.95 (26.88)
Search Engine Supply Index3.88 (0.95)

This Compound (39.30)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other36 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]