metobromuron profile

Metobromuron is a phenylurea herbicide used to control weeds in a variety of crops, including wheat, barley, and sugar beets. It is a selective herbicide, meaning that it is toxic to certain plants but not to others. Metobromuron works by inhibiting photosynthesis in susceptible plants, preventing them from producing the energy they need to grow. It is absorbed by plants through their roots and leaves and is translocated throughout the plant. Metobromuron is relatively persistent in the soil and can leach into groundwater. It is also toxic to aquatic organisms. The synthesis of metobromuron involves the reaction of 3-chloro-4-methylaniline with methyl isocyanate. This reaction produces a phenylurea compound, which is then reacted with bromine to produce the final product, metobromuron. Metobromuron is studied because it is a widely used herbicide and there is concern about its environmental impact. Studies have shown that metobromuron can have negative effects on aquatic organisms and that it can accumulate in the food chain. It is also important to study the effects of metobromuron on human health, as it can be absorbed through the skin and may cause irritation. Metobromuron's importance lies in its effectiveness as a herbicide, but its environmental and health concerns are under investigation and warrant further research.'

metobromuron: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	18290
CHEMBL ID	1356637
CHEBI ID	81964
SCHEMBL ID	53871
MeSH ID	M0052919

Synonym
urea, 3-(p-bromophenyl)-1-methoxy-1-methyl-
urea, n'-(4-bromophenyl)-n-methoxy-n-methyl-
metobromuron, analytical standard
NCGC00166156-01
metobromurone
metbromuron
3-(p-bromophenyl)-1-methoxy-1-methylurea
ciba-3126
brn 2103964
3-(p-bromophenyl)-1-methyl-1-methoxyurea
3-(4-bromphenyl)-1-methoxyharnstoff [german]
monobromuron
metobromuron
3-(4-bromophenyl)-1-methoxy-1-methylurea
einecs 221-301-5
hsdb 1741
n'-(4-bromophenyl)-n-methoxy-n-methylurea
n-(4-bromophenyl)-n'-methyl-n'-methoxy-harnstoff [german]
ccris 6765
patoran
metobromuron [ansi:bsi:iso]
caswell no. 579a
epa pesticide chemical code 035901
pattonex
c-3126
AKOS001609255
1-(4-bromophenyl)-3-methoxy-3-methylurea
dndi1246791
chebi:81964 ,
CHEMBL1356637
C18793
unii-4251089p3l
n-(4-bromophenyl)-n'-methyl-n'-methoxy-harnstoff
3-(4-bromphenyl)-1-methoxyharnstoff
4251089p3l ,
cas-3060-89-7
dtxsid6042157 ,
NCGC00255893-01
tox21_301964
dtxcid4022157
3060-89-7
FT-0603626
metobromuron [mi]
metobromuron [hsdb]
metobromuron [iso]
SCHEMBL53871
WLFDQEVORAMCIM-UHFFFAOYSA-N
n-(p-bromophenyl)-n'-methyl-n'-methoxyurea
patoran fl
metobromuron, pestanal(r), analytical standard
metobromuron 100 microg/ml in acetonitrile
metobromuron 10 microg/ml in acetonitrile
J-018035
Q18213352
Z1269144452
CS-0783319
HY-154817

Excerpt	Reference	Relevance
"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

Class	Description
ureas
[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)
Chain A, TYROSYL-DNA PHOSPHODIESTERASE	Homo sapiens (human)	Potency	56.2341	0.0040	23.8416	100.0000	AID485290
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	27.3060	0.0060	38.0041	19,952.5996	AID1159521; AID1159523
AR protein	Homo sapiens (human)	Potency	19.3312	0.0002	21.2231	8,912.5098	AID743054
nuclear receptor subfamily 1, group I, member 3	Homo sapiens (human)	Potency	51.3119	0.0010	22.6508	76.6163	AID1224838; AID1224839; AID1224893
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	48.9662	0.0002	14.3764	60.0339	AID720692
retinoic acid nuclear receptor alpha variant 1	Homo sapiens (human)	Potency	38.6720	0.0030	41.6115	22,387.1992	AID1159552; AID1159553; AID1159555
estrogen-related nuclear receptor alpha	Homo sapiens (human)	Potency	76.9588	0.0015	30.6073	15,848.9004	AID1224848; AID1224849
farnesoid X nuclear receptor	Homo sapiens (human)	Potency	0.4897	0.3758	27.4851	61.6524	AID743217
pregnane X nuclear receptor	Homo sapiens (human)	Potency	38.5708	0.0054	28.0263	1,258.9301	AID1346982
estrogen nuclear receptor alpha	Homo sapiens (human)	Potency	15.3553	0.0002	29.3054	16,493.5996	AID743080; AID743091
aryl hydrocarbon receptor	Homo sapiens (human)	Potency	42.5603	0.0007	23.0674	1,258.9301	AID743085; AID743122
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a	Homo sapiens (human)	Potency	17.2289	0.0017	23.8393	78.1014	AID743083
histone deacetylase 9 isoform 3	Homo sapiens (human)	Potency	24.3365	0.0376	17.0823	61.1927	AID1259364; AID1259388
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	5 (33.33)	18.7374
1990's	3 (20.00)	18.2507
2000's	5 (33.33)	29.6817
2010's	2 (13.33)	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]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	3 (18.75%)	4.05%
Observational	0 (0.00%)	0.25%
Other	13 (81.25%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	2.17	1	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	2	1	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
alachlor alachlor : An aromatic amide that is N-(2,6-diethylphenyl)acetamide substituted by a methoxymethyl group at at the nitrogen atom while one of the hydrogens of the methyl group has been replaced by a chlorine atom.	1.96	1	aromatic amide; monocarboxylic acid amide; organochlorine compound	environmental contaminant; herbicide; xenobiotic
chlorpropham Chlorpropham: A carbamate that is used as an herbicide and as a plant growth regulator.. chlorpropham : A carbamate ester that is the isopropyl ester of 3-chlorophenylcarbamic acid.	2.87	4	benzenes; carbamate ester; monochlorobenzenes	herbicide; plant growth retardant
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.	2.41	2	3-(3,4-substituted-phenyl)-1,1-dimethylurea; dichlorobenzene	environmental contaminant; mitochondrial respiratory-chain inhibitor; photosystem-II inhibitor; urea herbicide; xenobiotic
metolachlor metolachlor: structure given in first source. metolachlor : A racemate that consists of equimolar amounts of (R)- and (S)-metolachlor.. 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide : An organochlorine compound that is 2-chloroacetamide substituted by a (2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl) group at the nitrogen atom.	2.4	2	aromatic amide; benzenes; ether; organochlorine compound
propachlor propachlor: structure. propachlor : An anilide that consists of 2-chloroacetanilide bearing an N-isopropyl substituent.	1.96	1	anilide; monocarboxylic acid amide; organochlorine compound	environmental contaminant; herbicide; xenobiotic
simazine Simazine: A triazine herbicide.. simazine : A diamino-1,3,5-triazine that is N,N'-diethyl-1,3,5-triazine-2,4-diamine substituted by a chloro group at position 6.	1.95	1	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
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.	1.96	1	(trifluoromethyl)benzenes; C-nitro compound; substituted aniline	agrochemical; environmental contaminant; herbicide; xenobiotic
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	6.98	1	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
3,4-dichloroaniline 3,4-dichloroaniline : A dichloroaniline having the two chloro-substituents at the 3- and 4-positions.	2	1	dichloroaniline	epitope; xenobiotic
4-bromoaniline 4-bromoaniline: RN given refers to parent cpd; structure given in Merck Index, 9th ed, #1403	2	1
monuron monuron: minor descriptor (72-83); on-line & Index Medicus search UREA/AA (72-74) & HERBICIDES (72-74) & HERBICIDES UREA (75-83); RN given refers to unlabeled cpd; structure. monuron : 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 p-chlorophenyl group while the other is substituted by two methyl groups.	2	1	3-(3,4-substituted-phenyl)-1,1-dimethylurea; monochlorobenzenes	environmental contaminant; herbicide; xenobiotic
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	2.01	1	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
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.	2.67	3	dichlorobenzene; phenylureas	agrochemical; environmental contaminant; herbicide; xenobiotic
neburon neburon: structure in Merck Index, 9th ed, #6264	2	1	ureas
diphenamid diphenamid: do not confuse with anti-inflammatory agent difenpiramide; structure	1.96	1	diarylmethane
nitrofen nitrofen: structure	1.95	1	organic molecular entity	EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
siduron [no description available]	2	1	ureas
fluometuron fluometuron: RN given refers to parent cpd; structure. fluometuron : 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-(trifluoromethyl)phenyl group while the other is substituted by two methyl groups. It is a herbicide used for the control of broadleaf weeds and annual grasses in cotton.	2	1	(trifluoromethyl)benzenes; 3-(3,4-substituted-phenyl)-1,1-dimethylurea	agrochemical; environmental contaminant; herbicide; photosystem-II inhibitor; xenobiotic
terbacil terbacil: RN given refers to parent cpd; structure	2	1	organohalogen compound; pyrimidines
chlorbromuron chlorbromuron: structure	2.65	3	ureas
methoxuron 3-(3-chloro-4-methoxyphenyl)-1,1-dimethylurea: structure in first source. 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).	2.02	1	3-(3,4-substituted-phenyl)-1,1-dimethylurea; monochlorobenzenes; monomethoxybenzene	agrochemical; environmental contaminant; herbicide; photosystem-II inhibitor; plant growth regulator; xenobiotic
metribuzin metribuzin : A member of the class of 1,2,4-triazines that is 1,2,4-triazin-5(4H)-one substituted by an amino group at position 4, tert-butyl group at position 6 and a methylsulfanyl group at position 3.	2.01	1	1,2,4-triazines; cyclic ketone; organic sulfide	agrochemical; environmental contaminant; herbicide; xenobiotic
clomazone clomazone: an herbicide. clomazone : An isoxazolidinone that is 1,2-oxazolidin-3-one substituted by a 2-chlorobenzyl group at position 2 and two methyl groups at position 4.	2.01	1	isoxazolidinone; monochlorobenzenes	agrochemical; carotenoid biosynthesis inhibitor; environmental contaminant; herbicide; xenobiotic
oxazolidin-2-one Oxazolidinones: Derivatives of oxazolidin-2-one. They represent an important class of synthetic antibiotic agents.. oxazolidin-2-one : An oxazolidinone that is 1,3-oxazolidine with an oxo substituent at position 2.. oxazolidinone : An oxazolidine containing one or more oxo groups.	2.01	1	carbamate ester; oxazolidinone	metabolite
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.05	1	cyclodextrin
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	2.01	1	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient

Condition	Relationship Strength	Studies
Cyanosis A bluish or purplish discoloration of the skin and mucous membranes due to an increase in the amount of deoxygenated hemoglobin in the blood or a structural defect in the hemoglobin molecule.	1.98	1
Methemoglobinemia The presence of methemoglobin in the blood, resulting in cyanosis. A small amount of methemoglobin is present in the blood normally, but injury or toxic agents convert a larger proportion of hemoglobin into methemoglobin, which does not function reversibly as an oxygen carrier. Methemoglobinemia may be due to a defect in the enzyme NADH methemoglobin reductase (an autosomal recessive trait) or to an abnormality in hemoglobin M (an autosomal dominant trait). (Dorland, 27th ed)	2.69	3
Complications, Pregnancy [description not available]	1.98	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	1.98	1
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	7	1
Acute Disease Disease having a short and relatively severe course.	2	1

metobromuron

Description

Cross-References

Synonyms (57)

Research Excerpts

Toxicity

Drug Classes (1)

Protein Targets (13)

Potency Measurements

Research

Studies (15)

Market Indicators

Research Demand Index: 30.99

Study Types