CHEBI:38728 - monocrotophos

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ChEBI Name monocrotophos
ChEBI ID CHEBI:38728
Definition An alkenyl phosphate that is the 4-(methylamino)-4-oxobut-2-en-2-yl ester of dimethyl phosphate.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB1325292, eMolecules:486473, ZINC000000402767
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Atrazine is a chlorinated herbicide of the triazine class. It is used to prevent pre-emergence broadleaf weeds in crops such as maize (corn), soybean and sugarcane and on turf, such as golf courses and residential lawns. Atrazine's primary manufacturer is Syngenta and it is one of the most widely used herbicides in the United States, Canadian, and Australian agriculture. Its use was banned in the European Union in 2004, when the EU found groundwater levels exceeding the limits set by regulators, and Syngenta could not show that this could be prevented nor that these levels were safe. At least two significant Canadian farm well studies showed that atrazine was the most common contaminant found. As of 2001, atrazine was the most commonly detected pesticide contaminating drinking water in the U.S.: 44  Studies suggest it is an endocrine disruptor, an agent that can alter the natural hormonal system. However, in 2006 the U.S. Environmental Protection Agency (EPA) had stated that under the Food Quality Protection Act "the risks associated with the pesticide residues pose a reasonable certainty of no harm", and in 2007, the EPA said that atrazine does not adversely affect amphibian sexual development and that no additional testing was warranted. The EPA's 2009 review concluded that "the agency's scientific bases for its regulation of atrazine are robust and ensure prevention of exposure levels that could lead to reproductive effects in humans". However, in their 2016 Refined Ecological Risk Assessment for Atrazine, it was stated that "it is difficult to make definitive conclusions about the impact of atrazine at a given concentration but multiple studies have reported effects to various endpoints at environmentally-relevant concentrations." EPA started a registration review in 2013. The EPA's review has been criticized, and the safety of atrazine remains controversial. EPA has however stated that "If at any time EPA determines there are urgent human or environmental risks from atrazine exposure that require prompt attention, we will take appropriate regulatory action, regardless of the status of the registration review process."
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Formula C7H14NO5P
Net Charge 0
Average Mass 223.16356
Monoisotopic Mass 223.06096
InChI InChI=1S/C7H14NO5P/c1-6(5-7(9)8-2)13-14(10,11-3)12-4/h5H,1-4H3,(H,8,9)/b6-5+
InChIKey KRTSDMXIXPKRQR-AATRIKPKSA-N
SMILES CNC(=O)\C=C(/C)OP(=O)(OC)OC
Roles Classification
Biological Role(s): EC 3.1.1.7 (acetylcholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
EC 3.1.1.8 (cholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
EC 1.4.3.4 (monoamine oxidase) inhibitor
An EC 1.4.3.* (oxidoreductase acting on donor CH-NH2 group, oxygen as acceptor) inhibitor that interferes with the action of monoamine oxidase (EC 1.4.3.4).
Application(s): acaricide
A substance used to destroy pests of the subclass Acari (mites and ticks).
agrochemical
An agrochemical is a substance that is used in agriculture or horticulture.
avicide
A substance used to destroy bird pests (class Aves).
insecticide
Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.
(via organophosphorus insecticide )
pesticide
Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.
(via organophosphorus pesticide )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing monocrotophos (CHEBI:38728) has role acaricide (CHEBI:22153)
monocrotophos (CHEBI:38728) has role agrochemical (CHEBI:33286)
monocrotophos (CHEBI:38728) has role avicide (CHEBI:33289)
monocrotophos (CHEBI:38728) has role EC 1.4.3.4 (monoamine oxidase) inhibitor (CHEBI:38623)
monocrotophos (CHEBI:38728) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
monocrotophos (CHEBI:38728) has role EC 3.1.1.8 (cholinesterase) inhibitor (CHEBI:37733)
monocrotophos (CHEBI:38728) is a alkenyl phosphate (CHEBI:37494)
monocrotophos (CHEBI:38728) is a dialkyl phosphate (CHEBI:16648)
monocrotophos (CHEBI:38728) is a monocarboxylic acid amide (CHEBI:29347)
monocrotophos (CHEBI:38728) is a organophosphate insecticide (CHEBI:25708)
IUPAC Name
dimethyl (1E)-1-methyl-3-(methylamino)-3-oxoprop-1-en-1-yl phosphate
Synonyms Sources
(E)-monocrotophos HMDB
Azodrin ChemIDplus
Dimethyl (E)-1-methyl-2-(methylcarbamoyl)vinyl phosphate ChemIDplus
Dimethyl (E)-3-hydroxy-N-methylcrotonamide ChemIDplus
Phosphoric acid, dimethyl (E)-1-methyl-3-(methylamino)-3-oxo-1-propenyl ester ChemIDplus
Manual Xrefs Databases
1111 PPDB
C18663 KEGG COMPOUND
HMDB0031805 HMDB
Monocrotophos Wikipedia
View more database links
Registry Numbers Types Sources
2331934 Beilstein Registry Number Beilstein
6923-22-4 CAS Registry Number NIST Chemistry WebBook
6923-22-4 CAS Registry Number ChemIDplus
8415832 Reaxys Registry Number Reaxys
Citations Types Sources
23010531 PubMed citation Europe PMC
23228476 PubMed citation Europe PMC
23948368 PubMed citation Europe PMC
24105069 PubMed citation Europe PMC
24440807 PubMed citation Europe PMC
Last Modified
28 July 2014