Product Name

  • Name

    Acetochlor

  • EINECS 251-899-3
  • CAS No. 34256-82-1
  • Article Data13
  • CAS DataBase
  • Density 1.119 g/cm3
  • Solubility 222.8mg/L(temperature not stated)
  • Melting Point <0 °C
  • Formula C14H20ClNO2
  • Boiling Point 391.5 °C at 760 mmHg
  • Molecular Weight 269.771
  • Flash Point 190.5 °C
  • Transport Information UN 3082 9/PG 3
  • Appearance Brown liquid
  • Safety 2-36/37-60-61
  • Risk Codes 20-37/38-43-50/53
  • Molecular Structure Molecular Structure of 34256-82-1 (Acetochlor)
  • Hazard Symbols HarmfulXn, DangerousN
  • Synonyms Erunit;Acetamide, 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)-;2-Chloro-2-methyl-6-ethyl-N-ethoxymethylacetanilide;Harness;EPA Pesticide Chemical Code 121601;Acetochlore [ISO-French];Nevirex;2-chloro-N-ethoxymethyl-6, -ethylacet-o-toluidide;2-Chloro-N-(ethoxymethyl)-6-ethyl-o-acetotoluidide;Acetamide, 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)- (9CI);2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide;Acenit;Acetamide,2-chloro-N-(ethoxymethyl)-N-(2- ethyl-6-methylphenyl)-;Chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide;o-Acetotoluidide, 2-chloro-N-(ethoxymethyl)-6-ethyl- (8CI);
  • PSA 29.54000
  • LogP 3.12320

Synthetic route

C12H19NO

C12H19NO

chloroacetyl chloride
79-04-9

chloroacetyl chloride

Acetochlor
34256-82-1

Acetochlor

Conditions
ConditionsYield
In Petroleum ether for 5h; Reflux; Green chemistry; Industrial scale;91%
N-(2-methyl-6-ethyl)-phenyl-N-ethyloxymethyl-carbamoyl chloride
56917-59-0

N-(2-methyl-6-ethyl)-phenyl-N-ethyloxymethyl-carbamoyl chloride

chloroacetic acid
79-11-8

chloroacetic acid

Acetochlor
34256-82-1

Acetochlor

Conditions
ConditionsYield
In water; benzene82%
2-chloro-2'-ethyl-6'-methylacetanilide
32428-71-0

2-chloro-2'-ethyl-6'-methylacetanilide

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

Acetochlor
34256-82-1

Acetochlor

Conditions
ConditionsYield
With sodium hydroxide; PEG-400 In benzene at 15℃; for 2h; Yield given;
2-chloro-N-(ethoxymethyl)-N-(2-ethyl-4-iodo-6-methylphenyl)acetamide
161499-20-3

2-chloro-N-(ethoxymethyl)-N-(2-ethyl-4-iodo-6-methylphenyl)acetamide

Acetochlor
34256-82-1

Acetochlor

Conditions
ConditionsYield
With hydrogen; triethylamine; palladium on activated charcoal In ethanol for 3h; Ambient temperature;14 mg
pyridine
110-86-1

pyridine

Acetochlor
34256-82-1

Acetochlor

N'-pyridinium chloride

N'-pyridinium chloride

piperidine
110-89-4

piperidine

Acetochlor
34256-82-1

Acetochlor

N-ethoxymethyl-N-(piperidinylacetyl)-2-ethyl-6-methylbenzeneamine

N-ethoxymethyl-N-(piperidinylacetyl)-2-ethyl-6-methylbenzeneamine

Conditions
ConditionsYield
In ethanol for 3h; Substitution; Heating;
3,4-dichlorothiophenol
5858-17-3

3,4-dichlorothiophenol

Acetochlor
34256-82-1

Acetochlor

2-(3,4-dichloro-phenylsulfanyl)-N-ethoxymethyl-N-(2-ethyl-6-methyl-phenyl)-acetamide

2-(3,4-dichloro-phenylsulfanyl)-N-ethoxymethyl-N-(2-ethyl-6-methyl-phenyl)-acetamide

Conditions
ConditionsYield
With sodium carbonate In ethanol; water for 0.5h; Substitution; Heating;
Acetochlor
34256-82-1

Acetochlor

2,3,6-trimethyl-beta-cyclodextrin
55216-11-0

2,3,6-trimethyl-beta-cyclodextrin

C63H112O35*C14H20ClNO2
1448818-09-4

C63H112O35*C14H20ClNO2

Conditions
ConditionsYield
In water at 20℃; for 8h;

Acetochlor Chemical Properties

Molecular Formula: C14H20ClNO2
Molecular Weight: 269.77
MP: <0°C
Density: 1.119 g/cm3  
Flash Point: 190.5 °C 
Boiling Point: 391.5 °C at 760 mmHg 
storage temp.:  0-6°C
Vapour Pressure: 2.46E-06 mmHg at 25°C 
Index of Refraction: 1.538 
Appearance：Amber to purple transparent liquid
Solubility: 23 mg/L at 25°C in water. Acetochlor (CAS NO.34256-82-1) is soluble in alcohol, acetone, toluene and tetrachloride.
Stability：Acetochlor (CAS NO.34256-82-1) is stable under normal temperatures and pressures and is stable in neutral, weakly acidic and weakly alkaline media.

Acetochlor Uses

Acetochlor (CAS NO.34256-82-1) is a selective herbicide used for control of most annual grasses and certain broadleaf weeds. The effect in soil can persist for more than 8 weeks. It can be used on peanuts, corn, soybeans, maize, cotton, sunflower, vineyards, onion, green peas, potatoes etc.. Acetochlor (CAS NO.34256-82-1) is applied preemergence, preplant incorporated and is compatible with most other pesticides and fluid fertilizers when used at recommended rates.

Acetochlor Production

First, 2,6-methylethyl aniline, monochloroacetic acid react with trichloride to form 6-methylethyl-chloroacetyloy for aniline; then in the presence of hydrochloric acid, POM reacts with ethanol to form chloromethyl ethyl ether by etherification. Finally, Acetochlor (34256-82-1) is synthesized from 6-methylethyl-chloroacetyloy for aniline and chloromethyl ethyl ether by condensation.

Acetochlor Toxicity Data With Reference

1.    

orl-rat LD50:763 mg/kg

     PRKHDK    Problemi na Khigienata. Problems in Hygiene. 15 (1990),96.
2.    

orl-rbt LD50:600 mg/kg

     GISAAA    Gigiena i Sanitariya. 53 (5)(1988),84.

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 1550mg/kg (1550mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 29(12), Pg. 53, 1985.
rabbit LD50 oral 600mg/kg (600mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(5), Pg. 84, 1988.
rabbit LDLo skin 1260mg/kg (1260mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LIVER: OTHER CHANGES

BEHAVIORAL: FOOD INTAKE (ANIMAL)		 National Technical Information Service. Vol. OTS0536766,
rat LD50 intraperitoneal 1200mg/kg (1200mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 29(12), Pg. 53, 1985.
rat LD50 oral 763mg/kg (763mg/kg)   Problemi na Khigienata. Problems in Hygiene. Vol. 15, Pg. 96, 1990.

Acetochlor Safety Profile

Hazard Codes: NDangerous,XnHarmful (Harmful; Dangerous for the environment)
Risk Statements: 20-37/38-43-50/53 (Harmful by inhalation; Irritating to respiratory system and skin; May cause sensitization by skin contact; Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment)
Safety Statements: 2-36/37-60-61 (Keep out of the reach of children; Wear suitable protective clothing and gloves; This material and/or its container must be disposed of as hazardous waste; Avoid release to the environment)
RIDADR: UN3082 9/PG 3
RTECS: AB5457000
Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NOx and Cl−.

Acetochlor Standards and Recommendations

Content of Acetochlor (w/w): ≥95%
Water Content (w/w): ≤0.4%
Acidity (Calculated as H2SO4) (w/w): ≤0.1%

Acetochlor Specification

 Acetochlor is a herbicide developed by Monsanto Company and Zeneca. It is a member of the class of herbicides known as chloroacetanilides. Its mode of action is elongase inhibition, and inhibition of geranylgeranyl pyrophosphate (GGPP) cyclisation enzymes, part of the gibberellin pathway. It carries high risks of environmental contamination.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 0.0 deg C   EXP
log P (octanol-water) 3.03 (none)   EXP
Water Solubility 223 mg/L 25 EXP
Vapor Pressure 2.80E-05 mm Hg 25 EST
Henry's Law Constant 2.23E-08 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.96E-11 cm3/molecule-sec 25 EST


 

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