Page last updated: 2024-09-22

metazachlor

Description

metazachlor: alpha-chloroacetamide herbicide [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

metazachlor : An organochlorine compound that is 2-chloroacetamide substituted by a 2,6-dimethylphenyl and a (1H-pyrazol-1-ylmethyl) group at the nitrogen atom. [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 CID49384
CHEMBL ID2272118
CHEBI ID6798
SCHEMBL ID55016
MeSH IDM0512465

Synonyms (48)

Synonym
acetamide, 2-chloro-n-(2,6-dimethylphenyl)-n-(1h-pyrazol-1-ylmethyl)-
bas 479h
metazachlore
2-chloro-n-(pyrazol-1-ylmethyl)acet-2',6'-xylidide
2-chloro-n-(2,6-dimethylphenyl)-n-(1h-pyrazol-1-ylmethyl)-acetamide
2-chloro-n-(2,6-dimethylphenyl)-n-(1h-pyrazol-1-ylmethyl)acetamide
metazachlore [iso-french]
einecs 266-583-0
metazachlor [bsi:iso]
butisan s
brn 0621550
metazachlor
67129-08-2
2-chloro-n-(2,6-dimethylphenyl)-n-(pyrazol-1-ylmethyl)acetamide
FT-0658709
A835640
tpy2k437o4 ,
5-23-04-00126 (beilstein handbook reference)
unii-tpy2k437o4
pree
AKOS015915018
CHEMBL2272118
chebi:6798 ,
metazachlor [mi]
metazachlor [iso]
2-chloro-2',6'-dimethyl-n-(pyrazol-1-ylmethyl)acetanilide
SCHEMBL55016
EG-0202
2-chloro-2',6'-dimethyl-n-(pyrazol-1-yl-methyl)-acetanilide
DTXSID4058156
bas 47900h
metazochlor
W-104729
n-((1h-pyrazol-1-yl)methyl)-2-chloro-n-(2,6-dimethylphenyl)acetamide
us9138393, metazachlor
us9144538, metazachlor
bdbm181131
metazachlor, pestanal(r), analytical standard
metazachlor 100 microg/ml in acetone
metazachlor 100 microg/ml in acetonitrile
mfcd00055509
Q15834927
D97499
CS-0128829
HY-136373
2-chloro-n-(2,6-dimethylphenyl)-n-[(1h-pyrazol-1-yl)methyl]acetamide
EN300-6486517
Z3234906187

Research Excerpts

Overview

ExcerptReference
"Metazachlor is a chloroacetamide herbicide, frequently used in Brassica napus cultivations around the world. "( Biermans, G; Cuypers, A; Horemans, N; Koleva, L; Vangronsveld, J; Vassilev, A; Vercampt, H, 2016)
"Metazachlor is a frequently used herbicide with concentrations in surface waters up to 100 microg L(-1). "( Berghahn, R; Feibicke, M; Mohr, S; Schmidt, R; Schmiediche, R, 2008)

Roles (3)

RoleDescription
environmental contaminantAny minor or unwanted substance introduced into the environment that can have undesired effects.
xenobioticA xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
herbicideA substance used to destroy plant pests.
[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
aromatic amideAn amide in which the amide linkage is bonded directly to an aromatic system.
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
pyrazoles
[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]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1105321Herbicidal activity against Triticum aestivum (wheat) assessed as inhibition of root growth at 200 ug/ml relative to control2011Molecules (Basel, Switzerland), Mar-30, Volume: 16, Issue:4
Synthesis and herbicidal activity of 5-(4-hydroxybenzyl)-2-thioxoimidazolidin-4-one esters.
AID1105322Herbicidal activity against Triticum aestivum (wheat) assessed as inhibition of height growth at 200 ug/ml relative to control2011Molecules (Basel, Switzerland), Mar-30, Volume: 16, Issue:4
Synthesis and herbicidal activity of 5-(4-hydroxybenzyl)-2-thioxoimidazolidin-4-one esters.
AID1105323Herbicidal activity against Zea mays (maize) assessed as inhibition of root growth at 200 ug/ml relative to control2011Molecules (Basel, Switzerland), Mar-30, Volume: 16, Issue:4
Synthesis and herbicidal activity of 5-(4-hydroxybenzyl)-2-thioxoimidazolidin-4-one esters.
AID1105320Herbicidal activity against Arabidopsis thaliana assessed as inhibition of seed germination at 200 ug/ml relative to control2011Molecules (Basel, Switzerland), Mar-30, Volume: 16, Issue:4
Synthesis and herbicidal activity of 5-(4-hydroxybenzyl)-2-thioxoimidazolidin-4-one esters.
AID1105324Herbicidal activity against Zea mays (maize) assessed as inhibition of height growth at 200 ug/ml relative to control2011Molecules (Basel, Switzerland), Mar-30, Volume: 16, Issue:4
Synthesis and herbicidal activity of 5-(4-hydroxybenzyl)-2-thioxoimidazolidin-4-one esters.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (11.11)29.6817
2010's17 (62.96)24.3611
2020's7 (25.93)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other27 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (1)

ArticleYear
Short-term phytotoxicity in Brassica napus (L.) in response to pre-emergently applied metazachlor: A microcosm study.
Environmental toxicology and chemistry, Volume: 36, Issue: 1
2017
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (1)

ArticleYear
Effects of the herbicide metazachlor on macrophytes and ecosystem function in freshwater pond and stream mesocosms.
Aquatic toxicology (Amsterdam, Netherlands), May-01, Volume: 82, Issue: 2
2007
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]