ContaminantDB: Alachlor

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (26)XML

Record Information

Version

1.0

Creation Date

2009-06-05 16:50:55 UTC

Update Date

2026-03-25 19:42:46 UTC

Accession Number

CHEM000722

Identification

Common Name

Alachlor

Class

Small Molecule

Description

Selective preemergent herbicide used on food crops. Alachlor belongs to the family of Anilides. These are organic compounds derived fromA oxoacidsA RkE(=O)l(OH)mA (lA a 0) by replacing anA OHA group by theA NHPh group or derivative formed by ring substitution.

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HPV EPA Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Aromatic Hydrocarbon
Chloroacetanilide
Ether
Food Toxin
Herbicide
Household Toxin
Metabolite
Organic Compound
Organochloride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Chloro-2',6'-diethyl-N-(methoxymethyl)acetanilide	ChEBI
Alachlore	ChEBI
Chloressigsaeure-N-(methoxymethyl)-2,6-diaethylanilid	ChEBI
2-Chloro-2',6'-diethyl-N-(methoxymethyl)-acetanilde	HMDB
2-Chloro-2',6'-diethyl-N-(methoxymethyl)-acetanilide	HMDB
2-Chloro-N-(2,6-diethyl)phenyl-N-methoxymethylacetamide	HMDB
2-Chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide	HMDB
2-Chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide, 9ci	HMDB
Alachlor (pesticides mixture)	HMDB
Alachlor technical	HMDB
Alachlor technical (90% or more)	HMDB
Alachlor-atrazine	HMDB
Alagan	HMDB
Alanex	HMDB
Alanox	HMDB
Alapaz	HMDB
Alatox	HMDB
Alatox 480	HMDB
Alazine	HMDB
Alochlor	HMDB
alpha-Chloro-2',6'-diethyl-N-methoxymethylacetanilide	HMDB
Bullet	HMDB
Chimiclor	HMDB
Lasagrin	HMDB
Lasso	HMDB
Lasso micro-tech	HMDB
LAZO	HMDB
Metachlor	HMDB
Methachlor	HMDB
N-(Methoxymethyl)-2,6-diethylchloroacetanilide	HMDB
Nitala	HMDB
Pillarzo	HMDB
Ralchlor	HMDB
Satochlor	HMDB

Chemical Formula

C₁₄H₂₀ClNO₂

Average Molecular Mass

269.767 g/mol

Monoisotopic Mass

269.118 g/mol

CAS Registry Number

15972-60-8

IUPAC Name

2-chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide

Traditional Name

LAZO

SMILES

CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl

InChI Identifier

InChI=1S/C14H20ClNO2/c1-4-11-7-6-8-12(5-2)14(11)16(10-18-3)13(17)9-15/h6-8H,4-5,9-10H2,1-3H3

InChI Key

XCSGPAVHZFQHGE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Anilides

Alternative Parents

Substituents

Anilide
Tertiary carboxylic acid amide
Chloroacetamide
Carboxamide group
Carboxylic acid derivative
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Alkyl halide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:2533 )
organochlorine compound (CHEBI:2533 )
aromatic amide (CHEBI:2533 )
Anilide herbicides (C10928 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

herbicide

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White or cream, combustible crystalline solid without odour (5).

Experimental Properties

Property	Value
Melting Point	39.5 - 41.5°C
Boiling Point	Not Available
Solubility	0.24 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	3.02	ALOGPS
logP	3.59	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	16.6	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	73.93 m³·mol⁻¹	ChemAxon
Polarizability	29.02 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-Q (Non-derivatized)	splash10-01ot-4910000000-ff5ad7c7837234075e25	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-Q (Non-derivatized)	splash10-01ot-4910000000-ff5ad7c7837234075e25	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002e-2920000000-dc1318cf39b8cbc3d666	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0090000000-76b89888ca7d0dff5c1f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03dr-0980000000-72e2d13ea4c43a94533e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0900000000-5c144b05f6018cf50939	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000t-0900000000-56b06a1a995b2c236499	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001j-0900000000-b98598f80d6ddd013591	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0090000000-e48533a29dd990b17755	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0079-0090000000-be0d02d4b380f4f063df	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0290000000-d7e61817ec9dfb84134e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0930000000-85d33b07118012dc094f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0900000000-b439203d9ae3a2a94832	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-01ot-0900000000-1600624b1a228581c9a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000t-0900000000-3b284f85190209d4389b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0079-0090000000-80bab76e1cf9264266b6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0290000000-2f3b95987691a2f9a12c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0940000000-5490cf74e6d00907000a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0900000000-94c892fa0e45237f0550	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-01ot-0900000000-0782fe7afd5462ce19df	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000t-0900000000-b2dc4713e5954edf161b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0090000000-b8b7a2656098ef9720bb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0190000000-36c0adeceb429e1c87f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ki-1970000000-00709cc03ab9293da23a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-003r-2900000000-18c9f8b1a32719243006	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0190000000-0bfaa7611ca17634a1a7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-030c-3980000000-9c1c38c1a30035de4c0f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-076s-5910000000-d53d48694591a95583f2	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-8920000000-d26b3a61eea50f146512	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

oral (5) ; dermal (5)

Mechanism of Toxicity

Its mode of action is elongase inhibition, and inhibition of geranylgeranyl pyrophosphate (GGPP) cyclisation enzymes. It is also know to inhibit biosynthesis of fatty acids, lipids, protein, isoprenoids, flavonoids, and gibberellins. (4, 6).

Metabolism

Alachlor is metabolized and eliminated as conjugates of mercapturic acid, glucuronic acid, and sulfate in the urine and feces (7).

Toxicity Values

LD50: 930 - 1360 mg/kg (Oral, Rat) (5) LD50: 13 300 mg/kg (Dermal, Rabbit) (5)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

It is used mainly to control annual grasses and broadleaf weeds in corn (maize), soybeans, and peanuts (4).

Minimum Risk Level

Not Available

Health Effects

ARDS/acute lung injury, burns of the esophagus or gastrointestinal tract can result from acetochlor poisoning (8).

Symptoms

Alachlor is mildly irritating to the skin and eyes. Exposure to metalaxyl often results in such nonspecific symptoms as headache, dizziness, weakness, and nausea. Alachlor poisoning can produce an allergic hypersensitivity dermatitis or asthma with bronchospasm and wheezing with chronic exposure (8).

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0031766

FooDB ID

FDB008439

Phenol Explorer ID