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]
ID Source | ID |
---|---|
PubMed CID | 47445 |
CHEMBL ID | 1394379 |
CHEBI ID | 39388 |
SCHEMBL ID | 23700 |
MeSH ID | M0081793 |
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 |
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.
Excerpt | Reference | Relevance |
---|---|---|
"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 |
Excerpt | Reference | Relevance |
---|---|---|
"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 |
Excerpt | Relevance | Reference |
---|---|---|
" 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 |
Class | Description |
---|---|
benzoylurea insecticide | |
monochlorobenzenes | Any member of the class of chlorobenzenes containing a mono- or poly-substituted benzene ring in which only one substituent is chlorine. |
organofluorine compound | An organofluorine compound is a compound containing at least one carbon-fluorine bond. |
aromatic ether | Any 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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Chain A, TYROSYL-DNA PHOSPHODIESTERASE | Homo sapiens (human) | Potency | 7.9433 | 0.0040 | 23.8416 | 100.0000 | AID485290 |
nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 4.1036 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224893 |
retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 30.6379 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159555 |
pregnane X nuclear receptor | Homo sapiens (human) | Potency | 0.9689 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 0.1723 | 0.0002 | 29.3054 | 16,493.5996 | AID743080 |
aryl hydrocarbon receptor | Homo sapiens (human) | Potency | 14.0968 | 0.0007 | 23.0674 | 1,258.9301 | AID743085; AID743122 |
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 2.1690 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
activating transcription factor 6 | Homo sapiens (human) | Potency | 0.0012 | 0.1434 | 27.6121 | 59.8106 | AID1159516 |
histone deacetylase 9 isoform 3 | Homo sapiens (human) | Potency | 34.3762 | 0.0376 | 17.0823 | 61.1927 | AID1259364 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1090606 | Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 1 mg/L at 25 +/- 1 degC measured after 4 days | 2007 | Journal 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. |
AID1080629 | Insecticidal 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 method | 2009 | Journal of agricultural and food chemistry, May-13, Volume: 57, Issue:9 | Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas. |
AID1090609 | Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 10 mg/L at 25 +/- 1 degC measured after 4 days | 2007 | Journal 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. |
AID1090603 | Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 100 mg/L at 25 +/- 1 degC measured after 4 days | 2007 | Journal 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. |
AID1080637 | Insecticidal 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 days | 2009 | Journal of agricultural and food chemistry, May-13, Volume: 57, Issue:9 | Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas. |
AID1090607 | Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 2.5 mg/L at 25 +/- 1 degC measured after 4 days | 2007 | Journal 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. |
AID1090605 | Larvicidal activity against Mythimna separata (Oriental armyworm ) in compound treated corn leaves at 0.5 mg/L at 25 +/- 1 degC measured after 4 days | 2007 | Journal 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. |
AID1090604 | Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 0.25 mg/L at 25 +/- 1 degC measured after 4 days | 2007 | Journal 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. |
AID1080644 | Insecticidal 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 days | 2009 | Journal of agricultural and food chemistry, May-13, Volume: 57, Issue:9 | Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas. |
AID1080630 | Insecticidal 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 method | 2009 | Journal of agricultural and food chemistry, May-13, Volume: 57, Issue:9 | Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas. |
AID1080643 | Insecticidal 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 days | 2009 | Journal of agricultural and food chemistry, May-13, Volume: 57, Issue:9 | Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas. |
AID1080642 | Insecticidal 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 days | 2009 | Journal of agricultural and food chemistry, May-13, Volume: 57, Issue:9 | Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas. |
AID1090611 | Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 50 mg/L at 25 +/- 1 degC measured after 4 days | 2007 | Journal 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. |
AID1090608 | Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 5 mg/L at 25 +/- 1 degC measured after 4 days | 2007 | Journal 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. |
AID1090610 | Larvicidal activity against Mythimna separata (Oriental armyworm) in compound treated corn leaves at 25 mg/L at 25 +/- 1 degC measured after 4 days | 2007 | Journal 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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 18 (26.47) | 18.7374 |
1990's | 11 (16.18) | 18.2507 |
2000's | 16 (23.53) | 29.6817 |
2010's | 16 (23.53) | 24.3611 |
2020's | 7 (10.29) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (39.24) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 1 (1.41%) | 5.53% |
Reviews | 2 (2.82%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 68 (95.77%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |