Page last updated: 2024-12-06

clofentezine

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

Description

Clofentezine is a tetrazole acaricide used to control spider mites in various crops. It is effective against a wide range of mites, including the two-spotted spider mite (Tetranychus urticae) and the European red mite (Panonychus ulmi). Clofentezine acts as a growth regulator, interfering with the molting process of mites and preventing them from reaching adulthood. It has a long residual activity and can persist in the environment for several weeks. The compound's synthesis involves a multi-step process that starts with the reaction of a substituted benzene derivative with hydrazine. The resulting compound is then reacted with a substituted benzoyl chloride to produce the final clofentezine molecule. Clofentezine is studied for its efficacy against various mite species, its persistence in the environment, and its potential for resistance development. It is also studied to assess its impact on non-target organisms and the potential for environmental contamination.'

clofentezine: acaricide, primarily a mite ovicide; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

clofentezine : A tetrazine that is 1,2,4,5-tetrazine in which both of the hydrogens have been replaced by o-chlorophenyl groups. [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 CID73670
CHEMBL ID17888
CHEBI ID39315
SCHEMBL ID74002
MeSH IDM0172024

Synonyms (51)

Synonym
AC-12667
bisclofentazine
CHEBI:39315 ,
3,6-bis(o-chlorophenyl)-1,2,4,5-tetrazine
clofentezine
3,6-bis(2-chlorophenyl)-1,2,4,5-tetrazine
74115-24-5
bisclofentazin
NCGC00163794-01
1,2,4,5-tetrazine, 3,6-bis(2-chlorophenyl)-
caswell no. 593a
epa pesticide chemical code 125501
apollo (pesticide)
acaristop
nc 21314
einecs 277-728-2
apollo 50w
panatac
NCGC00163794-02
CHEMBL17888
NCGC00163794-04
NCGC00163794-03
C18576
cas-74115-24-5
tox21_300904
NCGC00259237-01
tox21_201688
dtxcid703881
dtxsid9023881 ,
NCGC00254808-01
clofentezine [ansi:bsi:iso]
unii-js4u0r0033
js4u0r0033 ,
FT-0603205
AKOS015902583
clofentezine [mi]
nc-21314
bisclofentezin
clofentezine [iso]
SCHEMBL74002
CS-5202
HY-B2066
W-104432
clofentezine, pestanal(r), analytical standard
clofentezine 10 microg/ml in cyclohexane
pesticide4_clofentezine_c14h8cl2n4_1,2,4,5-tetrazine, 3,6-bis(2-chlorophenyl)-
Q2979540
AMY37209
ZCA11524
AS-76292
mfcd00143998

Research Excerpts

Treatment

Clofentezine treatments in the juvenile stages significantly delayed development of the mites. This delay increased with increasing dose but decreased as the mite developed.

ExcerptReferenceRelevance
"Clofentezine treatment at any other developmental stage of T."( The effects of clofentezine on life-table parameters in two-spotted spider mite Tetranychus urticae.
Marcic, D, 2003
)
1.39
"Clofentezine treatments in the juvenile stages significantly delayed development of the mites, and this delay increased with increasing dose but decreased as the mites developed."( Assessment of sublethal effects of clofentezine on life-table parameters in Hawthorn spider mite (Tetranychus viennensis).
Li, D; Shen, Z; Tian, J, 2006
)
1.33

Dosage Studied

ExcerptRelevanceReference
" The compounds were tested at their respective maximum field recommended concentration (MFRC), and, when strong lethal effects were observed, a dose-response assay with a dilution series of the MFRC was undertaken to calculate LC(50) values."( Compatibility of traditional and novel acaricides with bumblebees (Bombus terrestris): a first laboratory assessment of toxicity and sublethal effects.
Besard, L; Cuvelier, X; Mommaerts, V; Smagghe, G; Sterk, G; Vandeven, J, 2010
)
0.36
" For oral exposures via treated sugar water, the dose-response assay showed the LC(50) values for abamectin, bifenazate, bifenthrin and etoxazole to be 1/15 MFRC (1."( Compatibility of traditional and novel acaricides with bumblebees (Bombus terrestris): a first laboratory assessment of toxicity and sublethal effects.
Besard, L; Cuvelier, X; Mommaerts, V; Smagghe, G; Sterk, G; Vandeven, J, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
mite growth regulatornull
tetrazine acaricidenull
[role 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]

Drug Classes (3)

ClassDescription
organochlorine acaricideAny organochlorine pesticide that has been used as an acaricide.
monochlorobenzenesAny member of the class of chlorobenzenes containing a mono- or poly-substituted benzene ring in which only one substituent is chlorine.
tetrazine
[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 (22)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LuciferasePhotinus pyralis (common eastern firefly)Potency1.05640.007215.758889.3584AID1224835
pregnane X receptorRattus norvegicus (Norway rat)Potency7.94330.025127.9203501.1870AID651751
RAR-related orphan receptor gammaMus musculus (house mouse)Potency7.91960.006038.004119,952.5996AID1159521; AID1159523
GLI family zinc finger 3Homo sapiens (human)Potency53.98440.000714.592883.7951AID1259368
AR proteinHomo sapiens (human)Potency6.05710.000221.22318,912.5098AID743054
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency13.93640.001022.650876.6163AID1224838; AID1224839; AID1224893
progesterone receptorHomo sapiens (human)Potency27.22270.000417.946075.1148AID1346784
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency4.71660.003041.611522,387.1992AID1159552; AID1159553; AID1159555
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency13.37300.001530.607315,848.9004AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403
pregnane X nuclear receptorHomo sapiens (human)Potency32.60230.005428.02631,258.9301AID1346982; AID720659
estrogen nuclear receptor alphaHomo sapiens (human)Potency15.89390.000229.305416,493.5996AID1259244; AID1259248; AID1259383; AID743069; AID743075; AID743079; AID743080; AID743091
aryl hydrocarbon receptorHomo sapiens (human)Potency25.52010.000723.06741,258.9301AID743085; AID743122
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency4.90860.001723.839378.1014AID743083
activating transcription factor 6Homo sapiens (human)Potency0.27300.143427.612159.8106AID1159516
v-jun sarcoma virus 17 oncogene homolog (avian)Homo sapiens (human)Potency17.22520.057821.109761.2679AID1159528
thyroid hormone receptor beta isoform aHomo sapiens (human)Potency11.22020.010039.53711,122.0200AID588547
histone deacetylase 9 isoform 3Homo sapiens (human)Potency7.09580.037617.082361.1927AID1259364; AID1259388
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency7.69590.000627.21521,122.0200AID651741; AID720636
Voltage-dependent calcium channel gamma-2 subunitMus musculus (house mouse)Potency16.39900.001557.789015,848.9004AID1259244
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency16.39900.001551.739315,848.9004AID1259244
ATPase family AAA domain-containing protein 5Homo sapiens (human)Potency45.03980.011917.942071.5630AID651632; AID720516
Ataxin-2Homo sapiens (human)Potency42.33710.011912.222168.7989AID651632
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
cell population proliferationATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of B cell proliferationATPase family AAA domain-containing protein 5Homo sapiens (human)
nuclear DNA replicationATPase family AAA domain-containing protein 5Homo sapiens (human)
signal transduction in response to DNA damageATPase family AAA domain-containing protein 5Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorATPase family AAA domain-containing protein 5Homo sapiens (human)
isotype switchingATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of DNA replicationATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of isotype switching to IgG isotypesATPase family AAA domain-containing protein 5Homo sapiens (human)
DNA clamp unloadingATPase family AAA domain-containing protein 5Homo sapiens (human)
regulation of mitotic cell cycle phase transitionATPase family AAA domain-containing protein 5Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of cell cycle G2/M phase transitionATPase family AAA domain-containing protein 5Homo sapiens (human)
negative regulation of receptor internalizationAtaxin-2Homo sapiens (human)
regulation of translationAtaxin-2Homo sapiens (human)
RNA metabolic processAtaxin-2Homo sapiens (human)
P-body assemblyAtaxin-2Homo sapiens (human)
stress granule assemblyAtaxin-2Homo sapiens (human)
RNA transportAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingATPase family AAA domain-containing protein 5Homo sapiens (human)
ATP bindingATPase family AAA domain-containing protein 5Homo sapiens (human)
ATP hydrolysis activityATPase family AAA domain-containing protein 5Homo sapiens (human)
DNA clamp unloader activityATPase family AAA domain-containing protein 5Homo sapiens (human)
DNA bindingATPase family AAA domain-containing protein 5Homo sapiens (human)
RNA bindingAtaxin-2Homo sapiens (human)
epidermal growth factor receptor bindingAtaxin-2Homo sapiens (human)
protein bindingAtaxin-2Homo sapiens (human)
mRNA bindingAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
Elg1 RFC-like complexATPase family AAA domain-containing protein 5Homo sapiens (human)
nucleusATPase family AAA domain-containing protein 5Homo sapiens (human)
cytoplasmAtaxin-2Homo sapiens (human)
Golgi apparatusAtaxin-2Homo sapiens (human)
trans-Golgi networkAtaxin-2Homo sapiens (human)
cytosolAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
membraneAtaxin-2Homo sapiens (human)
perinuclear region of cytoplasmAtaxin-2Homo sapiens (human)
ribonucleoprotein complexAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID9201In vitro rate of inhibition of A-549 tumor cell growth at 10E-8 mol/L2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Synthesis and antitumor activity of s-tetrazine derivatives.
AID152836In vitro rate of inhibition of P388 tumor cell growth at 10E-7 mol/L2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Synthesis and antitumor activity of s-tetrazine derivatives.
AID1111812Insecticidal activity against Panonychus ulmi HS in plum tree leaf assessed as larvae mortality compound treated by spray application measured after 7 to 8 days treatment2011Pest management science, Oct, Volume: 67, Issue:10
Monitoring of spirodiclofen susceptibility in field populations of European red mites, Panonychus ulmi (Koch) (Acari: Tetranychidae), and the cross-resistance pattern of a laboratory-selected strain.
AID9199In vitro rate of inhibition of A-549 tumor cell growth at 10E-6 mol/L2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Synthesis and antitumor activity of s-tetrazine derivatives.
AID268089Antiproliferative activity against human A549 cell line at 0.01 umol/L by SRB method2006Bioorganic & medicinal chemistry letters, Jul-15, Volume: 16, Issue:14
Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives.
AID1111807Insecticidal activity against Panonychus ulmi HS in plum tree leaf assessed as egg mortality compound treated by spray application measured after 7 to 8 days treatment2011Pest management science, Oct, Volume: 67, Issue:10
Monitoring of spirodiclofen susceptibility in field populations of European red mites, Panonychus ulmi (Koch) (Acari: Tetranychidae), and the cross-resistance pattern of a laboratory-selected strain.
AID1104429Toxicity against worker Bombus terrestris (bumblebee) assessed as mortality at 150 mg a.i./l, po administered through pollen for 11 weeks measured everyday for 3 days followed by once a week for 11 weeks2010Pest management science, Jul, Volume: 66, Issue:7
Compatibility of traditional and novel acaricides with bumblebees (Bombus terrestris): a first laboratory assessment of toxicity and sublethal effects.
AID268086Antiproliferative activity against human A549 cell line at 10 umol/L by SRB method2006Bioorganic & medicinal chemistry letters, Jul-15, Volume: 16, Issue:14
Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives.
AID268087Antiproliferative activity against human A549 cell line at 1 umol/L by SRB method2006Bioorganic & medicinal chemistry letters, Jul-15, Volume: 16, Issue:14
Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives.
AID152834In vitro rate of inhibition of P388 tumor cell growth at 10E-5 mol/L2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Synthesis and antitumor activity of s-tetrazine derivatives.
AID268088Antiproliferative activity against human A549 cell line at 0.1 umol/L by SRB method2006Bioorganic & medicinal chemistry letters, Jul-15, Volume: 16, Issue:14
Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives.
AID1104458Toxicity against worker Bombus terrestris (bumblebee) assessed as mortality at 150 mg a.i./l, po administered through sugar water for 11 weeks measured everyday for 3 days followed by once a week for 11 weeks2010Pest management science, Jul, Volume: 66, Issue:7
Compatibility of traditional and novel acaricides with bumblebees (Bombus terrestris): a first laboratory assessment of toxicity and sublethal effects.
AID9197In vitro rate of inhibition of A-549 tumor cell growth at 10E-4 mol/L2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Synthesis and antitumor activity of s-tetrazine derivatives.
AID268094Antiproliferative activity against mouse P388 cell line at 0.01 umol/L by MTT method2006Bioorganic & medicinal chemistry letters, Jul-15, Volume: 16, Issue:14
Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives.
AID9198In vitro rate of inhibition of A-549 tumor cell growth at 10E-5 mol/L2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Synthesis and antitumor activity of s-tetrazine derivatives.
AID1104477Contact toxicity against worker Bombus terrestris (bumblebee) assessed as mortality at 150 mg a.i./l applied on the dorsal thorax for 11 weeks measured everyday for 3 days followed by once a week for 11 weeks2010Pest management science, Jul, Volume: 66, Issue:7
Compatibility of traditional and novel acaricides with bumblebees (Bombus terrestris): a first laboratory assessment of toxicity and sublethal effects.
AID268093Antiproliferative activity against mouse P388 cell line at 0.1 umol/L by MTT method2006Bioorganic & medicinal chemistry letters, Jul-15, Volume: 16, Issue:14
Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives.
AID1111793Insecticidal activity against Panonychus ulmi PSR-TK in plum tree leaf assessed as mortality at larvae stage compound treated by spray application measured after 7 to 8 days treatment2011Pest management science, Oct, Volume: 67, Issue:10
Monitoring of spirodiclofen susceptibility in field populations of European red mites, Panonychus ulmi (Koch) (Acari: Tetranychidae), and the cross-resistance pattern of a laboratory-selected strain.
AID152835In vitro rate of inhibition of P388 tumor cell growth at 10E-6 mol/L2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Synthesis and antitumor activity of s-tetrazine derivatives.
AID1104373Toxicity against worker Bombus terrestris (bumblebee) assessed as reduction in reproduction at 150 mg a.i./l, po administered through pollen for 11 weeks measured once a week for 11 weeks2010Pest management science, Jul, Volume: 66, Issue:7
Compatibility of traditional and novel acaricides with bumblebees (Bombus terrestris): a first laboratory assessment of toxicity and sublethal effects.
AID1111790Resistance ratio, LC50 for egg Panonychus ulmi HS to LC50 for egg Panonychus ulmi PSR TK2011Pest management science, Oct, Volume: 67, Issue:10
Monitoring of spirodiclofen susceptibility in field populations of European red mites, Panonychus ulmi (Koch) (Acari: Tetranychidae), and the cross-resistance pattern of a laboratory-selected strain.
AID1111787Resistance ratio, LC50 for adult Panonychus ulmi HS to LC50 for adult Panonychus ulmi GE 16/092011Pest management science, Oct, Volume: 67, Issue:10
Monitoring of spirodiclofen susceptibility in field populations of European red mites, Panonychus ulmi (Koch) (Acari: Tetranychidae), and the cross-resistance pattern of a laboratory-selected strain.
AID152837In vitro rate of inhibition of P388 tumor cell growth at 10E-8 mol/L2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Synthesis and antitumor activity of s-tetrazine derivatives.
AID1111789Resistance ratio, LC50 for larvae Panonychus ulmi HS to LC50 for larvae Panonychus ulmi PSR TK2011Pest management science, Oct, Volume: 67, Issue:10
Monitoring of spirodiclofen susceptibility in field populations of European red mites, Panonychus ulmi (Koch) (Acari: Tetranychidae), and the cross-resistance pattern of a laboratory-selected strain.
AID268091Antiproliferative activity against mouse P388 cell line at 10 umol/L by MTT method2006Bioorganic & medicinal chemistry letters, Jul-15, Volume: 16, Issue:14
Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives.
AID152833In vitro rate of inhibition of P388 tumor cell growth at 10E-4 mol/L2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Synthesis and antitumor activity of s-tetrazine derivatives.
AID268090Antiproliferative activity against mouse P388 cell line at 100 umol/L by MTT method2006Bioorganic & medicinal chemistry letters, Jul-15, Volume: 16, Issue:14
Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives.
AID268085Antiproliferative activity against human A549 cell line at 100 umol/L by SRB method2006Bioorganic & medicinal chemistry letters, Jul-15, Volume: 16, Issue:14
Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives.
AID1111792Insecticidal activity against Panonychus ulmi PSR-TK in plum tree leaf assessed as mortality at egg stage compound treated by spray application measured after 7 to 8 days treatment2011Pest management science, Oct, Volume: 67, Issue:10
Monitoring of spirodiclofen susceptibility in field populations of European red mites, Panonychus ulmi (Koch) (Acari: Tetranychidae), and the cross-resistance pattern of a laboratory-selected strain.
AID9200In vitro rate of inhibition of A-549 tumor cell growth at 10E-7 mol/L2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Synthesis and antitumor activity of s-tetrazine derivatives.
AID1104406Contact toxicity against worker Bombus terrestris (bumblebee) assessed as reduction in reproduction at 150 mg a.i./l applied on the dorsal thorax for 11 weeks measured once a week for 11 weeks relative to control2010Pest management science, Jul, Volume: 66, Issue:7
Compatibility of traditional and novel acaricides with bumblebees (Bombus terrestris): a first laboratory assessment of toxicity and sublethal effects.
AID268092Antiproliferative activity against mouse P388 cell line at 1 umol/L by MTT method2006Bioorganic & medicinal chemistry letters, Jul-15, Volume: 16, Issue:14
Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (7.14)18.7374
1990's2 (14.29)18.2507
2000's6 (42.86)29.6817
2010's5 (35.71)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: 33.74

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index33.74 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.93 (4.65)
Search Engine Demand Index63.12 (26.88)
Search Engine Supply Index3.09 (0.95)

This Compound (33.74)

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%
Other17 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]