Compounds > methoxuron
Page last updated: 2024-11-05

methoxuron

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

Description

Methoxuron is a phenylurea herbicide that acts as an inhibitor of photosynthesis. It is a selective herbicide used to control broadleaf weeds in cereal crops, such as wheat and barley. Methoxuron is applied as a pre-emergence herbicide, meaning it is applied to the soil before the weeds germinate. The synthesis of methoxuron involves a series of chemical reactions starting with the coupling of phenylurea and a substituted phenol. Methoxuron's effects include inhibiting the Hill reaction in chloroplasts, which prevents the production of ATP and NADPH, essential for photosynthesis. Its importance stems from its effectiveness in controlling a wide range of weeds, contributing to increased crop yields. Methoxuron is studied to investigate its potential for improving weed control strategies, understand its environmental impact, and develop new and more environmentally friendly herbicides. '

3-(3-chloro-4-methoxyphenyl)-1,1-dimethylurea: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

metoxuron : A member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which one of the nitrogens is substituted by a 3-chloro-4-methoxyphenyl group while the other is substituted by two methyl groups. It is a plant growth regulator and a pre- and post-emergence herbicide used for the control of grasses and broad-leaved weeds in carrots and cereals (e.g. wheat, barley and rye). [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 CID29863
CHEBI ID6907
SCHEMBL ID63260
MeSH IDM0105621

Synonyms (59)

Synonym
urea, n'-(3-chloro-4-methoxyphenyl)-n,n-dimethyl-
dosanex
19937-59-8
metoxuron
(3-chloro-4-methoxyphenyl)-n,n-dimethylurea
n,n-dimethyl-n'-(4-methoxy-3-chlorophenyl)urea
purivel
fl
san 6915h
caswell no. 194b
metoxuron [bsi:iso]
einecs 243-433-2
3-(3-chloro-4-methoxyphenyl)-1,1-dimethylurea
n-(3-chloro-4-methoxyphenyl)-n',n'-dimethylurea
brn 2128284
dosanex fl
dosagran
dosaflo
deftor
n'-(3-chlor-4-methoxy-phenyl)-n,n-dimethylharnstoff [german]
dosanex mg
epa pesticide chemical code 294600
herbicide 6602
urea, 3-(3-chloro-4-methoxyphenyl)-1,1-dimethyl-
3-(3-chlor-4-methoxyphenyl)-1,1-dimethylharnstoff [german]
sulerex
san 7102h
mx3 herbicide
n'-(3-chlor-4-methoxy-phenyl)-n,n-dimethylharnstoff
methoxuron
unii-y58em37e76
3-(3-chlor-4-methoxyphenyl)-1,1-dimethylharnstoff
4-13-00-01272 (beilstein handbook reference)
y58em37e76 ,
FT-0613611
AKOS015888423
SCHEMBL63260
n'-(3-chloro-4-methoxyphenyl)-n,n-dimethyl urea
metoxuron [iso]
1-(3-chloro-4-methoxyphenyl)-3,3-dimethylurea
san-7102
n'-(3-chloro-4-methoxyphenyl)-n,n-dimethylurea
metoxuran
san-6602
investt
CHEBI:6907
san 6602
DSRNRYQBBJQVCW-UHFFFAOYSA-N
n'-(3-chloro-4-methoxyphenyl)-n,n-dimethylurea #
san 7102
3-(3-chloro-4-methoxy-phenyl)-1,1-dimethyl-urea
DTXSID1042158
metoxuron, pestanal(r), analytical standard
metoxuron 100 microg/ml in acetonitrile
metoxuron 10 microg/ml in acetonitrile
J-012876
Q22808428
3-(3-chloro-4-methoxylphenyl)-1,1-dimethylurea
dosanex; metoxuran;purivel; san 6602; san 7102

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Halogenated phenylurea herbicides are not very toxic by themselves to animals, but their exposure to UV light may significantly increase the toxicity of their solutions."( Influence of UV irradiation on the toxicity of phenylurea herbicides using Microtox test.
Bonnemoy, F; Boulkamh, A; Lavédrine, B, 2004)		0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (6)

RoleDescription
agrochemicalAn agrochemical is a substance that is used in agriculture or horticulture.
environmental contaminantAny minor or unwanted substance introduced into the environment that can have undesired effects.
herbicideA substance used to destroy plant pests.
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.
photosystem-II inhibitornull
plant growth regulatorA chemical, natural or artificial, that can affect the rate of growth of a plant.
[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
3-(3,4-substituted-phenyl)-1,1-dimethylureaA member of the class of phenylureas that is urea in which one of the nitrogens is substituted by two methyl groups while the other is substituted by a phenyl group which carries two unspecified groups at positions 3 and 4 of the phenyl ring.
monomethoxybenzeneCompounds containing a benzene skeleton substituted with one methoxy group.
monochlorobenzenesAny member of the class of chlorobenzenes containing a mono- or poly-substituted benzene ring in which only one substituent is chlorine.
[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]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (30.00)18.7374
1990's0 (0.00)18.2507
2000's6 (60.00)29.6817
2010's1 (10.00)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: 11.54

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 Index11.54 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.03 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.54)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (10.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
glycine
[no description available]		2.2110alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical
2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one
2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one: from maize extracts; structure given in first source. DIMBOA : A lactol that is DIBOA in which the hydrogen at position 7 is replaced by a methoxy group. It has been isolated from the maize plants.		2.0310aromatic ether;
benzoxazine;
cyclic hydroxamic acid;
lactol		allelochemical;
plant metabolite
dimethoate
Dimethoate: An organothiophosphorus cholinesterase inhibitor that is used as a systemic and contact insecticide.. dimethoate : A monocarboxylic acid amide that is N-methylacetamide in which one of the hydrogens of the methyl group attached to the carbonyl moiety is replaced by a (dimethoxyphosphorothioyl)sulfanediyl group.		1.9710monocarboxylic acid amide;
organic thiophosphate		acaricide;
agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
environmental contaminant;
insecticide;
xenobiotic
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.		2.02103-(3,4-substituted-phenyl)-1,1-dimethylurea;
dichlorobenzene		environmental contaminant;
mitochondrial respiratory-chain inhibitor;
photosystem-II inhibitor;
urea herbicide;
xenobiotic
ifosfamide
[no description available]		3.3911ifosfamidesalkylating agent;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
xenobiotic
malathion
Malathion: A wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes.. malathion : A racemate comprising equimolar amounts of (R) and (S)-malathion. It is a broad spectrum organophosphate proinsecticide used to control a wide range of pests including Coleoptera, Diptera, fruit flies, mosquitos and spider mites.. diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate : A diester that is diethyl succinate in which position 2 is substituted by a (dimethoxyphosphorothioyl)thio group.		2.2110diester;
ethyl ester;
organic thiophosphate
trifluralin
Trifluralin: A microtubule-disrupting pre-emergence herbicide.. trifluralin : A substituted aniline that is N,N-dipropylaniline substituted by a nitro groups at positions 2 and 6 and a trifluoromethyl group at position 4. It is an agrochemical used as a pre-emergence herbicide.		1.9710(trifluoromethyl)benzenes;
C-nitro compound;
substituted aniline		agrochemical;
environmental contaminant;
herbicide;
xenobiotic
diquat
Diquat: A contact herbicide used also to produce desiccation and defoliation. (From Merck Index, 11th ed). diquat : The organic cation formed formally by addition of an ethylene bridge between the nitrogen atoms of 2,2'-bipyridine. Most often available as the dibromide.		2.4320organic cationdefoliant;
herbicide
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.		1.9710dichlorobenzene;
phenylureas		agrochemical;
environmental contaminant;
herbicide;
xenobiotic
metobromuron
metobromuron: structure		2.0210ureas
chlortoluron
chlorotoluron : A member of the class of phenylureas that is urea in which one of the nitrogens is substituted by two methyl groups while the other is substituted by a 3-chloro-4-methylphenyl group. A herbicide that is non-toxic to honeybees but moderately toxic to mammals, birds, earthworms and most aquatic organisms.		210monochlorobenzenes;
phenylureas		agrochemical;
environmental contaminant;
herbicide;
xenobiotic
2,4-dihydroxy-1,4-benzoxazin-3-one
2,4-dihydroxy-1,4-benzoxazin-3-one: structure in first source. DIBOA : A lactol that consists of 1,4-benzoxazine bearing two hydroxy substituents at positions 2 and 4 as well as a keto group at position 3.		2.0310benzoxazine;
cyclic hydroxamic acid;
lactol		allelochemical;
herbicide;
phytotoxin;
plant metabolite
fenitrothion
Fenitrothion: An organothiophosphate cholinesterase inhibitor that is used as an insecticide.. fenitrothion : An organic thiophosphate that is O,O-dimethyl O-phenyl phosphorothioate substituted by a methyl group at position 3 and a nitro group at position 4.		1.9710C-nitro compound;
organic thiophosphate		acaricide;
agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
insecticide
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		3.3911taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		2.02101,2,3-triazole
carfentrazone-ethyl
carfentrazone-ethyl: structure in first source. carfentrazone-ethyl : A racemate comprising equimolar amounts of (R)- and (S)-carfentrazone-ethylcarfentrazone-ethyl. A proherbicide for the herbicide carfentrazone (by hydrolysis of the ester group to the corresponding acid), it is used to control broad-leafed weeds in potatoes and cereal crops.. ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate : An ethyl ester resulting from the formal condensation of the carboxy group of 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoic acid with ethanol.		2.0210ethyl esterproherbicide
terics
terics: medicated blocks used for control of cattle bloat; RN given is for teric N; nonylphenol ethoxylate is resistant to environmental breakdown so EPA discourages use		2.0310
mevinphos
Mevinphos: An organophosphate cholinesterase inhibitor that is used as an insecticide.		1.9710
ConditionIndicatedRelationship StrengthStudiesTrials
Female Genital Neoplasms
[description not available]		03.3911
Cancer of Pelvis
[description not available]		03.3911
Genital Neoplasms, Female
Tumor or cancer of the female reproductive tract (GENITALIA, FEMALE).		03.3911
Neutropenia
A decrease in the number of NEUTROPHILS found in the blood.		03.3911