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clofentezine : A tetrazine that is 1,2,4,5-tetrazine in which both of the hydrogens have been replaced by o-chlorophenyl groups.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]
ID Source | ID |
---|---|
PubMed CID | 73670 |
CHEMBL ID | 17888 |
CHEBI ID | 39315 |
SCHEMBL ID | 74002 |
MeSH ID | M0172024 |
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 |
Clofentezine treatments in the juvenile stages significantly delayed development of the mites. This delay increased with increasing dose but decreased as the mite developed.
Excerpt | Reference | Relevance |
---|---|---|
"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 |
Excerpt | Relevance | Reference |
---|---|---|
" 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 |
Role | Description |
---|---|
mite growth regulator | null |
tetrazine acaricide | null |
[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] |
Class | Description |
---|---|
organochlorine acaricide | Any organochlorine pesticide that has been used as an acaricide. |
monochlorobenzenes | Any 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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Luciferase | Photinus pyralis (common eastern firefly) | Potency | 1.0564 | 0.0072 | 15.7588 | 89.3584 | AID1224835 |
pregnane X receptor | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 0.0251 | 27.9203 | 501.1870 | AID651751 |
RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 7.9196 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521; AID1159523 |
GLI family zinc finger 3 | Homo sapiens (human) | Potency | 53.9844 | 0.0007 | 14.5928 | 83.7951 | AID1259368 |
AR protein | Homo sapiens (human) | Potency | 6.0571 | 0.0002 | 21.2231 | 8,912.5098 | AID743054 |
nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 13.9364 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
progesterone receptor | Homo sapiens (human) | Potency | 27.2227 | 0.0004 | 17.9460 | 75.1148 | AID1346784 |
retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 4.7166 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159553; AID1159555 |
estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 13.3730 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403 |
pregnane X nuclear receptor | Homo sapiens (human) | Potency | 32.6023 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982; AID720659 |
estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 15.8939 | 0.0002 | 29.3054 | 16,493.5996 | AID1259244; AID1259248; AID1259383; AID743069; AID743075; AID743079; AID743080; AID743091 |
aryl hydrocarbon receptor | Homo sapiens (human) | Potency | 25.5201 | 0.0007 | 23.0674 | 1,258.9301 | AID743085; AID743122 |
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 4.9086 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
activating transcription factor 6 | Homo sapiens (human) | Potency | 0.2730 | 0.1434 | 27.6121 | 59.8106 | AID1159516 |
v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 17.2252 | 0.0578 | 21.1097 | 61.2679 | AID1159528 |
thyroid hormone receptor beta isoform a | Homo sapiens (human) | Potency | 11.2202 | 0.0100 | 39.5371 | 1,122.0200 | AID588547 |
histone deacetylase 9 isoform 3 | Homo sapiens (human) | Potency | 7.0958 | 0.0376 | 17.0823 | 61.1927 | AID1259364; AID1259388 |
nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 7.6959 | 0.0006 | 27.2152 | 1,122.0200 | AID651741; AID720636 |
Voltage-dependent calcium channel gamma-2 subunit | Mus musculus (house mouse) | Potency | 16.3990 | 0.0015 | 57.7890 | 15,848.9004 | AID1259244 |
Glutamate receptor 2 | Rattus norvegicus (Norway rat) | Potency | 16.3990 | 0.0015 | 51.7393 | 15,848.9004 | AID1259244 |
ATPase family AAA domain-containing protein 5 | Homo sapiens (human) | Potency | 45.0398 | 0.0119 | 17.9420 | 71.5630 | AID651632; AID720516 |
Ataxin-2 | Homo sapiens (human) | Potency | 42.3371 | 0.0119 | 12.2221 | 68.7989 | AID651632 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Process | via Protein(s) | Taxonomy |
---|---|---|
protein binding | ATPase family AAA domain-containing protein 5 | Homo sapiens (human) |
ATP binding | ATPase family AAA domain-containing protein 5 | Homo sapiens (human) |
ATP hydrolysis activity | ATPase family AAA domain-containing protein 5 | Homo sapiens (human) |
DNA clamp unloader activity | ATPase family AAA domain-containing protein 5 | Homo sapiens (human) |
DNA binding | ATPase family AAA domain-containing protein 5 | Homo sapiens (human) |
RNA binding | Ataxin-2 | Homo sapiens (human) |
epidermal growth factor receptor binding | Ataxin-2 | Homo sapiens (human) |
protein binding | Ataxin-2 | Homo sapiens (human) |
mRNA binding | Ataxin-2 | Homo sapiens (human) |
[Information is prepared from geneontology information from the June-17-2024 release] |
Process | via Protein(s) | Taxonomy |
---|---|---|
plasma membrane | Glutamate receptor 2 | Rattus norvegicus (Norway rat) |
Elg1 RFC-like complex | ATPase family AAA domain-containing protein 5 | Homo sapiens (human) |
nucleus | ATPase family AAA domain-containing protein 5 | Homo sapiens (human) |
cytoplasm | Ataxin-2 | Homo sapiens (human) |
Golgi apparatus | Ataxin-2 | Homo sapiens (human) |
trans-Golgi network | Ataxin-2 | Homo sapiens (human) |
cytosol | Ataxin-2 | Homo sapiens (human) |
cytoplasmic stress granule | Ataxin-2 | Homo sapiens (human) |
membrane | Ataxin-2 | Homo sapiens (human) |
perinuclear region of cytoplasm | Ataxin-2 | Homo sapiens (human) |
ribonucleoprotein complex | Ataxin-2 | Homo sapiens (human) |
cytoplasmic stress granule | Ataxin-2 | Homo sapiens (human) |
[Information is prepared from geneontology information from the June-17-2024 release] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID9201 | In vitro rate of inhibition of A-549 tumor cell growth at 10E-8 mol/L | 2004 | Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5 | Synthesis and antitumor activity of s-tetrazine derivatives. |
AID152836 | In vitro rate of inhibition of P388 tumor cell growth at 10E-7 mol/L | 2004 | Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5 | Synthesis and antitumor activity of s-tetrazine derivatives. |
AID1111812 | Insecticidal activity against Panonychus ulmi HS in plum tree leaf assessed as larvae mortality compound treated by spray application measured after 7 to 8 days treatment | 2011 | Pest 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. |
AID9199 | In vitro rate of inhibition of A-549 tumor cell growth at 10E-6 mol/L | 2004 | Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5 | Synthesis and antitumor activity of s-tetrazine derivatives. |
AID268089 | Antiproliferative activity against human A549 cell line at 0.01 umol/L by SRB method | 2006 | Bioorganic & 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. |
AID1111807 | Insecticidal activity against Panonychus ulmi HS in plum tree leaf assessed as egg mortality compound treated by spray application measured after 7 to 8 days treatment | 2011 | Pest 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. |
AID1104429 | Toxicity 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 weeks | 2010 | Pest 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. |
AID268086 | Antiproliferative activity against human A549 cell line at 10 umol/L by SRB method | 2006 | Bioorganic & 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. |
AID268087 | Antiproliferative activity against human A549 cell line at 1 umol/L by SRB method | 2006 | Bioorganic & 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. |
AID152834 | In vitro rate of inhibition of P388 tumor cell growth at 10E-5 mol/L | 2004 | Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5 | Synthesis and antitumor activity of s-tetrazine derivatives. |
AID268088 | Antiproliferative activity against human A549 cell line at 0.1 umol/L by SRB method | 2006 | Bioorganic & 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. |
AID1104458 | Toxicity 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 weeks | 2010 | Pest 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. |
AID9197 | In vitro rate of inhibition of A-549 tumor cell growth at 10E-4 mol/L | 2004 | Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5 | Synthesis and antitumor activity of s-tetrazine derivatives. |
AID268094 | Antiproliferative activity against mouse P388 cell line at 0.01 umol/L by MTT method | 2006 | Bioorganic & 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. |
AID9198 | In vitro rate of inhibition of A-549 tumor cell growth at 10E-5 mol/L | 2004 | Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5 | Synthesis and antitumor activity of s-tetrazine derivatives. |
AID1104477 | Contact 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 weeks | 2010 | Pest 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. |
AID268093 | Antiproliferative activity against mouse P388 cell line at 0.1 umol/L by MTT method | 2006 | Bioorganic & 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. |
AID1111793 | Insecticidal 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 treatment | 2011 | Pest 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. |
AID152835 | In vitro rate of inhibition of P388 tumor cell growth at 10E-6 mol/L | 2004 | Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5 | Synthesis and antitumor activity of s-tetrazine derivatives. |
AID1104373 | Toxicity 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 weeks | 2010 | Pest 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. |
AID1111790 | Resistance ratio, LC50 for egg Panonychus ulmi HS to LC50 for egg Panonychus ulmi PSR TK | 2011 | Pest 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. |
AID1111787 | Resistance ratio, LC50 for adult Panonychus ulmi HS to LC50 for adult Panonychus ulmi GE 16/09 | 2011 | Pest 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. |
AID152837 | In vitro rate of inhibition of P388 tumor cell growth at 10E-8 mol/L | 2004 | Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5 | Synthesis and antitumor activity of s-tetrazine derivatives. |
AID1111789 | Resistance ratio, LC50 for larvae Panonychus ulmi HS to LC50 for larvae Panonychus ulmi PSR TK | 2011 | Pest 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. |
AID268091 | Antiproliferative activity against mouse P388 cell line at 10 umol/L by MTT method | 2006 | Bioorganic & 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. |
AID152833 | In vitro rate of inhibition of P388 tumor cell growth at 10E-4 mol/L | 2004 | Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5 | Synthesis and antitumor activity of s-tetrazine derivatives. |
AID268090 | Antiproliferative activity against mouse P388 cell line at 100 umol/L by MTT method | 2006 | Bioorganic & 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. |
AID268085 | Antiproliferative activity against human A549 cell line at 100 umol/L by SRB method | 2006 | Bioorganic & 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. |
AID1111792 | Insecticidal 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 treatment | 2011 | Pest 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. |
AID9200 | In vitro rate of inhibition of A-549 tumor cell growth at 10E-7 mol/L | 2004 | Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5 | Synthesis and antitumor activity of s-tetrazine derivatives. |
AID1104406 | Contact 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 control | 2010 | Pest 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. |
AID268092 | Antiproliferative activity against mouse P388 cell line at 1 umol/L by MTT method | 2006 | Bioorganic & 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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 1 (7.14) | 18.7374 |
1990's | 2 (14.29) | 18.2507 |
2000's | 6 (42.86) | 29.6817 |
2010's | 5 (35.71) | 24.3611 |
2020's | 0 (0.00) | 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 moderate demand-to-supply ratio for research on this compound.
| This Compound (33.74) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 17 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |