Page last updated: 2024-12-06

triflumuron

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

Description

Triflumuron is an insecticide that belongs to the benzoylurea class. It acts as a chitin synthesis inhibitor, disrupting the development of insect exoskeletons and causing mortality. It is commonly used to control a wide range of insect pests, particularly in agriculture and public health. Triflumuron is synthesized via a multi-step process involving the reaction of benzoyl chloride with an appropriate amine. The synthesis typically involves the use of a catalyst and appropriate reaction conditions to optimize the yield and purity of the final product. The mode of action of triflumuron involves its interaction with chitin synthase, an enzyme responsible for the biosynthesis of chitin. Chitin is a major component of the insect exoskeleton, and by inhibiting its synthesis, triflumuron prevents insects from molting properly, leading to their death. Triflumuron has been extensively studied due to its effectiveness as an insecticide and its low mammalian toxicity. Research on triflumuron encompasses areas such as its efficacy against different insect pests, its environmental fate and persistence, and its potential for resistance development. The importance of studying triflumuron stems from its widespread use in pest control, the need to understand its environmental impact, and the potential for resistance development in target insect populations.'

triflumuron: insect growth inhibitor [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID47445
CHEMBL ID1394379
CHEBI ID39388
SCHEMBL ID23700
MeSH IDM0081793

Synonyms (55)

Synonym
bay-vi 7533
bay-sir 8514
einecs 264-980-3
benzamide, 2-chloro-n-(((4-(trifluoromethoxy)phenyl)amino)carbonyl)-
sir 8514
brn 2776684
epa pesticide chemical code 118201
triflumuron [iso]
alsystin
ai3-29368
2-chloro-n-(((4-(trifluoromethoxy)phenyl)amino)carbonyl)benzamide
alsystine
caswell no. 217c
oms 2015
mascot
2-chloro-n-({[4-(trifluoromethoxy)phenyl]amino}carbonyl)benzamide
2-chloro-n-{[4-(trifluoromethoxy)phenyl]carbamoyl}benzamide
triflumuron
CHEBI:39388 ,
1-(o-chlorobenzoyl)-3-(p-(trifluoromethoxy)phenyl)urea
64628-44-0
trifluron
NCGC00094568-02
NCGC00094568-01
SPECTRUM1505170
2-chloro-n-[[4-(trifluoromethoxy)phenyl]carbamoyl]benzamide
2-chloranyl-n-[[4-(trifluoromethyloxy)phenyl]carbamoyl]benzamide
2-chloro-n-[oxo-[4-(trifluoromethoxy)anilino]methyl]benzamide
A834834
C18615
tox21_301874
NCGC00255190-01
cas-64628-44-0
dtxsid5034355 ,
dtxcid3014355
3ft64dyg8k ,
unii-3ft64dyg8k
FT-0630748
AKOS015889501
SCHEMBL23700
CHEMBL1394379
triflumuron [mart.]
1-(2-chlorobenzoyl)-3-(4-trifluoromethoxyphenyl)urea
triflumuron [mi]
triflumuron, certified reference material, tracecert(r)
mfcd00072496
CCG-231010
benzamide, 2-chloro-n-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]-
triflumuron, pestanal(r), analytical standard
2-chloro-n-(4-(trifluoromethoxy)phenylcarbamoyl)benzamide
1-(2-chlorobenzoyl)-3-[4-(trifluoromethoxy)phenyl]urea
2-chloro-n-((4-(trifluoromethoxy)phenyl)carbamoyl)benzamide
AS-13364
Q1995523
E78670

Research Excerpts

Overview

Triflumuron (TFM) is a benzoyl phenyl urea insecticide belonging to the class of IGRs. It is commonly used in Tunisian agriculture to control crop pests and flies.

ExcerptReferenceRelevance
"Triflumuron (TFM) is a benzoyl phenyl urea insecticide belonging to the class of IGRs."( Mini-review highlighting toxic effects of triflumuron in insects and mammalian systems.
Abid-Essefi, S; Amara, I; Salem, IB; Souid, G; Timoumi, R, 2023
)
1.9
"Triflumuron (TFM) is a benzoylurea insecticide commonly used in Tunisian agriculture and around the world to control crop pests and flies as a promising alternative to conventional insecticides for its arthropod specificity and low toxicity. "( Metabolism of triflumuron in the human liver: Contribution of cytochrome P450 isoforms and esterases.
Abid-Essefi, S; Buratti, FM; Dorne, JCM; Testai, E; Timoumi, R, 2019
)
2.32

Toxicity

ExcerptReferenceRelevance
"The increased use of pesticides is the origin of multiple damages to the environment and to humans; thus, the search for new strategies to reduce or even protect the toxic effects caused by these synthetic products became a necessity."( Protective effects of fennel essential oil against oxidative stress and genotoxicity induced by the insecticide triflumuron in human colon carcinoma cells.
Abid-Essefi, S; Amara, I; Annabi, E; Salem, IB; Timoumi, R, 2020
)
0.77
" Among those compounds, we focused our interest on triflumuron (TFM), which is less toxic than other conventional insecticides."( Triflumuron induces cytotoxic effects on hepatic and renal human cell lines.
Abid-Essefi, S; Amara, I; Ben Salem, I; Timoumi, R, 2020
)
2.25
" As these compounds are potentially toxic to the target organisms, they could also be harmful to human health and the environment."( Mini-review highlighting toxic effects of triflumuron in insects and mammalian systems.
Abid-Essefi, S; Amara, I; Salem, IB; Souid, G; Timoumi, R, 2023
)
1.17

Dosage Studied

ExcerptRelevanceReference
" albopictus was evaluated with laboratory strains through dose-response assays."( Effect of triflumuron, a chitin synthesis inhibitor, on Aedes aegypti, Aedes albopictus and Culex quinquefasciatus under laboratory conditions.
Belinato, TA; Lima, JB; Martins, AJ; Valle, D, 2013
)
0.79
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
benzoylurea insecticide
monochlorobenzenesAny member of the class of chlorobenzenes containing a mono- or poly-substituted benzene ring in which only one substituent is chlorine.
organofluorine compoundAn organofluorine compound is a compound containing at least one carbon-fluorine bond.
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 (9)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency7.94330.004023.8416100.0000AID485290
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency4.10360.001022.650876.6163AID1224838; AID1224893
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency30.63790.003041.611522,387.1992AID1159552; AID1159555
pregnane X nuclear receptorHomo sapiens (human)Potency0.96890.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency0.17230.000229.305416,493.5996AID743080
aryl hydrocarbon receptorHomo sapiens (human)Potency14.09680.000723.06741,258.9301AID743085; AID743122
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency2.16900.001723.839378.1014AID743083
activating transcription factor 6Homo sapiens (human)Potency0.00120.143427.612159.8106AID1159516
histone deacetylase 9 isoform 3Homo sapiens (human)Potency34.37620.037617.082361.1927AID1259364
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID1090606Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 1 mg/L at 25 +/- 1 degC measured after 4 days2007Journal of agricultural and food chemistry, Apr-04, Volume: 55, Issue:7
Insecticidal benzoylphenylurea-S-carbamate: a new propesticide with two effects of both benzoylphenylureas and carbamates.
AID1080629Insecticidal activity against third-instar larval stage of Spodoptera exigua in cabbage leaves assessed as mortality at 25 +/-1degC treated for 5 secs before larval infestation measured after 4 days by leaf dip method2009Journal of agricultural and food chemistry, May-13, Volume: 57, Issue:9
Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas.
AID1090609Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 10 mg/L at 25 +/- 1 degC measured after 4 days2007Journal of agricultural and food chemistry, Apr-04, Volume: 55, Issue:7
Insecticidal benzoylphenylurea-S-carbamate: a new propesticide with two effects of both benzoylphenylureas and carbamates.
AID1090603Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 100 mg/L at 25 +/- 1 degC measured after 4 days2007Journal of agricultural and food chemistry, Apr-04, Volume: 55, Issue:7
Insecticidal benzoylphenylurea-S-carbamate: a new propesticide with two effects of both benzoylphenylureas and carbamates.
AID1080637Insecticidal activity against fourth-instar larval stage of Mythimna separata (Oriental armyworm) in compound-pretreated corn leaves assessed as mortality at 2.5 mg/l at 25 +/-1degC after 4 days2009Journal of agricultural and food chemistry, May-13, Volume: 57, Issue:9
Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas.
AID1090607Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 2.5 mg/L at 25 +/- 1 degC measured after 4 days2007Journal of agricultural and food chemistry, Apr-04, Volume: 55, Issue:7
Insecticidal benzoylphenylurea-S-carbamate: a new propesticide with two effects of both benzoylphenylureas and carbamates.
AID1090605Larvicidal activity against Mythimna separata (Oriental armyworm ) in compound treated corn leaves at 0.5 mg/L at 25 +/- 1 degC measured after 4 days2007Journal of agricultural and food chemistry, Apr-04, Volume: 55, Issue:7
Insecticidal benzoylphenylurea-S-carbamate: a new propesticide with two effects of both benzoylphenylureas and carbamates.
AID1090604Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 0.25 mg/L at 25 +/- 1 degC measured after 4 days2007Journal of agricultural and food chemistry, Apr-04, Volume: 55, Issue:7
Insecticidal benzoylphenylurea-S-carbamate: a new propesticide with two effects of both benzoylphenylureas and carbamates.
AID1080644Insecticidal activity against fourth-instar larval stage of Mythimna separata (Oriental armyworm) in compound-pretreated corn leaves assessed as mortality at 1 mg/l at 25 +/-1degC after 4 days2009Journal of agricultural and food chemistry, May-13, Volume: 57, Issue:9
Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas.
AID1080630Insecticidal activity against larvae of Plutella xylostella (diamondback moth) in cabbage leaves assessed as mortality at 25 +/-1degC treated for 5 secs before larval infestation measured after 4 days by leafdip method2009Journal of agricultural and food chemistry, May-13, Volume: 57, Issue:9
Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas.
AID1080643Insecticidal activity against fourth-instar larval stage of Mythimna separata (Oriental armyworm) in compound-pretreated corn leaves assessed as mortality at 0.5 mg/l at 25 +/-1degC after 4 days2009Journal of agricultural and food chemistry, May-13, Volume: 57, Issue:9
Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas.
AID1080642Insecticidal activity against fourth-instar larval stage of Mythimna separata (Oriental armyworm) in compound-pretreated corn leaves assessed as mortality at 0.25 mg/l at 25 +/-1degC after 4 days2009Journal of agricultural and food chemistry, May-13, Volume: 57, Issue:9
Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas.
AID1090611Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 50 mg/L at 25 +/- 1 degC measured after 4 days2007Journal of agricultural and food chemistry, Apr-04, Volume: 55, Issue:7
Insecticidal benzoylphenylurea-S-carbamate: a new propesticide with two effects of both benzoylphenylureas and carbamates.
AID1090608Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 5 mg/L at 25 +/- 1 degC measured after 4 days2007Journal of agricultural and food chemistry, Apr-04, Volume: 55, Issue:7
Insecticidal benzoylphenylurea-S-carbamate: a new propesticide with two effects of both benzoylphenylureas and carbamates.
AID1090610Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 25 mg/L at 25 +/- 1 degC measured after 4 days2007Journal of agricultural and food chemistry, Apr-04, Volume: 55, Issue:7
Insecticidal benzoylphenylurea-S-carbamate: a new propesticide with two effects of both benzoylphenylureas and carbamates.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (68)

TimeframeStudies, This Drug (%)All Drugs %
pre-199018 (26.47)18.7374
1990's11 (16.18)18.2507
2000's16 (23.53)29.6817
2010's16 (23.53)24.3611
2020's7 (10.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 39.24

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 Index39.24 (24.57)
Research Supply Index4.29 (2.92)
Research Growth Index4.62 (4.65)
Search Engine Demand Index62.36 (26.88)
Search Engine Supply Index2.27 (0.95)

This Compound (39.24)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.41%)5.53%
Reviews2 (2.82%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other68 (95.77%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]