Compounds > 3,4,3',4'-tetrachloroazoxybenzene
Page last updated: 2024-12-06

3,4,3',4'-tetrachloroazoxybenzene

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

Description

3,4,3',4'-Tetrachloroazoxybenzene, also known as TCAB, is a persistent organic pollutant (POP) that has been widely used as a fungicide and insecticide. It is synthesized through the reaction of 3,4-dichloroaniline with sodium nitrite in acidic conditions. TCAB is highly toxic to various organisms and has been found to bioaccumulate in food chains. Its persistence in the environment, its potential for bioaccumulation, and its toxicity have led to concerns about its impacts on human health and ecosystems. Research on TCAB focuses on its environmental fate and transport, its toxicological effects, and its remediation strategies. Studies have investigated its degradation pathways in different environmental compartments, its bioaccumulation in organisms, and its potential for causing endocrine disruption, cancer, and other adverse health effects. Further research is needed to better understand the long-term consequences of TCAB exposure and to develop effective strategies for its control and remediation.'
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3,4,3',4'-tetrachloroazoxybenzene: unwanted contaminant found in commercial synthesis of dichloroaniline or herbicides made from dichloroaniline; implicated in outbreak of acne in chemical workers [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID30533
MeSH IDM0060910

Synonyms (12)

Synonym
tcaob
bis(3,4-dichlorophenyl)diazene 1-oxide
azoxybenzene, 3,3',4,4'-tetrachloro-
diazene, bis(3,4-dichlorophenyl)-, 1-oxide
3,4,3',4'-tetrachloroazoxybenzene
ccris 3013
1,2-dichloro-4-(3,4-dichlorophenyl)-nno-azoxybenzene
3,3',4,4'-tetrachloroazoxybenzene
21232-47-3
(3,4-dichlorophenyl)-(3,4-dichlorophenyl)imino-oxidoazanium
DTXSID1026087
3,3',4,4'-tetrachloroazoxybenzene 100 microg/ml in acetonitrile

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Both TCAB and TCAOB were more toxic than all other chemicals that have been tested in the chick embryo with the exception of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)."( Embryotoxicity of 3,3',4,4'-tetrachloroazobenzene and 3,3',4,4'-tetrachloroazoxybenzene in the chick embryo.
Hsia, MT; Kreamer, BL; Schrankel, KR, 1982)		0.26

Bioavailability

ExcerptReferenceRelevance
" Absolute bioavailability was calculated to be approximately 9%."( Absorption and disposition kinetics of 3,3',4,4'-tetrachloroazoxybenzene in the male Fischer 344 rat.
Kattnig, MJ; Liebler, DC; Mayersohn, M; Pillai, UA; Sipes, IG; Smith, RL; Ziegler, TL, 1996)		0.29

Dosage Studied

ExcerptRelevanceReference
" In 2 groups of weanling rats the same dosage of TCAOB was able to reduce the relative thymus weight to 31% and 38% of the comparable control animals."( Thymic atrophy induced by acute exposure of 3,3',4,4'-tetrachloroazobenzene and 3,3',4,4'-tetrachloroazoxybenzene in rats.
Burant, CF; Hsia, MT; Kreamer, BL; Schrankel, KR, 1982)		0.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (77.27)18.7374
1990's4 (18.18)18.2507
2000's1 (4.55)29.6817
2010's0 (0.00)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: 11.14

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

MetricThis Compound (vs All)
Research Demand Index11.14 (24.57)
Research Supply Index3.18 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.14)

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%
Other23 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
diuron
Diuron: A pre-emergent herbicide.. diuron : A member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which both of the hydrogens attached to one nitrogen are substituted by methyl groups, and one of the hydrogens attached to the other nitrogen is substituted by a 3,4-dichlorophenyl group.		1.96103-(3,4-substituted-phenyl)-1,1-dimethylurea;
dichlorobenzene		environmental contaminant;
mitochondrial respiratory-chain inhibitor;
photosystem-II inhibitor;
urea herbicide;
xenobiotic
propanil
Propanil: A chlorinated anilide that is used as an herbicide.. propanil : An anilide resulting from the formal condensation of the carboxy group of propanoic acid with the amino group of 3,4-dichloroaniline. It is a herbicide used for the treatment of numerous grasses and broad-leaved weeds in rice, potatoes, and wheat.		2.3720anilide;
dichlorobenzene		herbicide
3,4-dichloroaniline
3,4-dichloroaniline : A dichloroaniline having the two chloro-substituents at the 3- and 4-positions.		1.9710dichloroanilineepitope;
xenobiotic
linuron
Linuron: A selective pre- and post-emergence herbicide. (From Merck Index, 11th ed). linuron : A member of the class of phenylureas that is N-methyl urea substituted by a methoxy group at position 1 and a 3,4-dichlorophenyl group at position 3.		1.9610dichlorobenzene;
phenylureas		agrochemical;
environmental contaminant;
herbicide;
xenobiotic
neburon
neburon: structure in Merck Index, 9th ed, #6264		1.9610ureas
3,4,3',4'-tetrachloroazobenzene
3,4,3',4'-tetrachloroazobenzene: unwanted contaminant found in commercial synthesis of dichloroaniline or herbicides made from dichloroaniline; implicated in outbreak of acne in chemical workers; RN given refers to parent cpd; structure		3.75110
3,4,3',4'-tetrachlorobiphenyl
3,4,3',4'-tetrachlorobiphenyl: RN given refers to parent cpd. 3,3',4,4'-tetrachlorobiphenyl : A tetrachlorobiphenyl that is biphenyl in which the hydrogens at position 3 and 4 on each phenyl group are replaced by chlorines.		1.9710dichlorobenzene;
tetrachlorobiphenyl
ConditionIndicatedRelationship StrengthStudiesTrials
Acne
[description not available]		02.3620
Dermatitis, Occupational
A recurrent contact dermatitis caused by substances found in the work place.		02.3620
Acne Vulgaris
A chronic disorder of the pilosebaceous apparatus associated with an increase in sebum secretion. It is characterized by open comedones (blackheads), closed comedones (whiteheads), and pustular nodules. The cause is unknown, but heredity and age are predisposing factors.		02.3620
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		03.2260
Aging
The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.		01.9610
Cleft Palate, Isolated
[description not available]		02.3720
Fetal Death
Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.		02.3720
Cleft Palate
Congenital fissure of the soft and/or hard palate, due to faulty fusion.		02.3720
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.6530
Anasarca
[description not available]		01.9610
Hydronephrosis
Abnormal enlargement or swelling of a KIDNEY due to dilation of the KIDNEY CALICES and the KIDNEY PELVIS. It is often associated with obstruction of the URETER or chronic kidney diseases that prevents normal drainage of urine into the URINARY BLADDER.		01.9610
Edema
Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.		01.9610
Atrophy
Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.		01.9610
Chromosome-Defective Micronuclei
[description not available]		0210
Keratoderma Blennorrhagicum
[description not available]		01.9610
Hyperplasia
An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.		01.9610
Keratosis
Any horny growth such as a wart or callus.		01.9610
Abnormalities, Autosome
[description not available]		01.9610