metolachlor [ANSI, WSSA]

Names

[ Name ]:
metolachlor [ANSI, WSSA]

[Synonym ]:
2-Chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide
Cotoran multi
2-Chloro-6'-ethyl-N-(2-methoxy-1-methylethyl)acet-o-toluidide
2R C1 BNV1GY1&1O1
2-chloro-N-(6-ethyl-o-tolyl)-N-[(1RS)-2-methoxy-1-methylethyl]acetamide
Primagram
2-chloro-6’-ethyl-N-[(1RS)-2-methoxy-1-methylethyl]acet-o-toluidide
Metolachlor
Bicep
Primextra
EINECS 257-060-8
Acetamide, 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)-
2-Chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide
2-Chloro-N-(2-ethyl-6-methylphenyl)-N-(-2-methoxy-1-methylethyl)acetamide
rac-2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(2R)-1-methoxypropan-2-yl]acetamide
MFCD00055293
α-Chloro-2'-ethyl-6'-methyl-N-(1-methyl-2-methoxyethyl)acetanilide
2-Chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxy-2-propanyl)acetamide

Biological Activity

[Description]:

Metolachlor is a pre-emergent selective, chloroacetanilide herbicide for the control of a variety of annual grass and broad leaf weeds in corn and other crops. Metolachlor is a chiral herbicide consisting of four stereoisomers[1][2].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[References]

[1]. Jingqian Xie, et al. Metolachlor Stereoisomers: Enantioseparation, Identification and Chiral Stability. J Chromatogr A. 2016 Sep 9;1463:42-8.

[2]. D M Stamper, et al. Biodegradation of the Acetanilide Herbicides Alachlor, Metolachlor, and Propachlor. Crit Rev Microbiol. 1998;24(1):1-22.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
406.8±45.0 °C at 760 mmHg

[ Melting Point ]:
-62.1 °C

[ Molecular Formula ]:
C₁₅H₂₂ClNO₂

[ Molecular Weight ]:
283.794

[ Flash Point ]:
199.8±28.7 °C

[ Exact Mass ]:
283.133911

[ PSA ]:
29.54000

[ LogP ]:
3.00

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.533

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AN3430000

CHEMICAL NAME :: o-Acetotoluidide, 2-chloro-6'-ethyl-N-(2-methoxy-1-methylethyl)-

CAS REGISTRY NUMBER :: 51218-45-2

LAST UPDATED :: 199701

DATA ITEMS CITED :: 23

MOLECULAR FORMULA :: C15-H22-Cl-N-O2

MOLECULAR WEIGHT :: 283.83

WISWESSER LINE NOTATION :: 2R C1 BNV1GY1&1O1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Open irritation test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1750 mg/m3/4H

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3170 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 620 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >9 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3170 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1150 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 410 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - duck

DOSE/DURATION :: >2510 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5460 mg/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 131 gm/kg/2Y-C

TOXIC EFFECTS :: Liver - other changes Liver - changes in liver weight Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 263 gm/kg/2Y-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 4550 mg/kg/26W-C

TOXIC EFFECTS :: Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10 gm/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 100 ug/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 281,295,1992 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H317

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R43

[ Safety Phrases ]:
S36/37

[ RIDADR ]:
UN1648 3/PG 2

[ RTECS ]:
AN3430000

[ HS Code ]:
2924299017

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299017

[ Summary ]:
2924299017 2-chloro-n-(2-ethyl-6-methylphenyl)-n-(1-methoxypropan-2-yl)acetamide。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:9.0%。MFN tarrif:6.5%。general tariff:30.0%

Articles

Embryotoxic and genotoxic effects of heavy metals and pesticides on early life stages of Pacific oyster (Crassostrea gigas).

Mar. Pollut. Bull. 64(12) , 2663-70, (2012)

This study evaluated embryotoxicity and genotoxicity of two dissolved metals copper and cadmium (Cu and Cd) and two pesticides (metolachlor and irgarol) occurring in Arcachon Bay (SW France) in Pacifi...

Polar organic chemical integrative samplers for pesticides monitoring: impacts of field exposure conditions.

Sci. Total Environ. 488-489 , 188-96, (2014)

This study focuses on how Polar Organic Chemical Integrative Samplers (POCIS) work in real environmental conditions. A selection of 23 polar pesticides and 8 metabolites were investigated by exposure ...

Biodegradation of the acetanilide herbicides alachlor, metolachlor, and propachlor.

Crit. Rev. Microbiol 24(1) , 1-22, (1998)

Alachlor, metolachlor, and propachlor are detoxified in biological systems by the formation of glutathione-acetanilide conjugates. This conjugation is mediated by glutathione-S-transferase, which is p...