34256-82-1

Basic information

• Product Name: Acetochlor
• Synonyms: SACEMID(R);SURPASS(R);TROPHY(R);2-CHLORO-N-ETHOXYMETHYL-6'-ETHYLACET-O-TOLUIDIDE;ACETOCHLOR;ACENITE(R);HARNESS;HARNESS PLUS(R)
• CAS NO: 34256-82-1
• Molecular Formula: C₁₄H₂₀ClNO₂
• Molecular Weight: 269.77
• EINECS: 251-899-3
• Product Categories: Agro-Chemicals;A-BAlphabetic;Alpha sort;Pesticides&Metabolites;2000/60/EC;A;AA to ALPesticides&Metabolites;Alphabetic;AmideMethod Specific;European Community: ISO and DIN;Herbicides
• Mol File: 34256-82-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: <0℃
• Boiling Point: bp0.4 torr 134°
• Flash Point: >68°C
• Appearance: Brown liquid
• Density: 1.1
• Vapor Pressure: 2.46E-06mmHg at 25°C
• Refractive Index: nD20 1.5272
• Storage Temp.: 0-6°C
• PKA: 1.29±0.50(Predicted)
• Water Solubility: 222.8mg/L(temperature not stated)
• BRN: 2859702
• CAS DataBase Reference: Acetochlor(CAS DataBase Reference)
• NIST Chemistry Reference: Acetochlor(34256-82-1)
• EPA Substance Registry System: Acetochlor(34256-82-1)

Safety Data

• Hazard Codes: Xn;N,N,Xn
• Statements: 20-37/38-43-50/53
• Safety Statements: 2-36/37-60-61
• RIDADR: UN3082 9/PG 3
• WGK Germany: 2
• RTECS: AB5457000
• Hazardous Substances Data: 34256-82-1(Hazardous Substances Data)

Usage

Description

Acetochlor is a member of the chloroacetanilide compounds. It is used as herbicide to control against grasses and broadleaf weeds in corn, soya beans, sorghum and peanuts grown in high organic content. It is applied to the soil as a pre- and post-emergence treatment. It is mainly absorbed by the roots and leaves, inhibiting protein synthesis in shoot meristems and root tips.

References

[1] N. Xiao, B. Jing, F. Ge and X. Liu, The fate of herbicide acetochlor and its toxicity to Eisenia fetida under laboratory conditions, Chemosphere, 2006, vol. 62, 1366-1373 [2] P. V. Sha and Angelo Moretto,? Acetochlor, WHO

Uses

Herbicide.

Definition

ChEBI: A monocarboxylic acid amide that is N-phenylacetamide carrying an ethyl and a methyl group at positions 2 and 6 respectively on the benzene ring while one of the methyl hydrogens as well as the hydrogen attached to the nitrogen atom have been replaced by a chloro and an ethoxymethyl group respectively.

Agricultural Uses

Herbicide: A U.S. EPA restricted Use Pesticide (RUP). Approval pending in the EU. A pre-emergence herbicide for control of annual grasses and broadleaf weeds. It is used on cabbage, citrus cops, coffee, all types of corn, cotton, green peas, maize, onion, peanuts, potatoes, vineyards, sugar cane, and sugar beets, among others. It is compatible with most other pesticides.

Trade name

ACENIT?; CP 55097?; DEGREE?; ERUNIT?; FULTIME?; GUARDIAN?; HARNESS?; KEYSTONE LA?; MG 02?; MON 097?; MON 58420?; NEVIREX?; RELAY?; SACEMID?; SURPASS?; TOPHAND?; TOPNOTCH?; TROPHEE?; TROPHY?; WINNER?

Metabolic pathway

The initial metabolism of acetochlor is investigated to delineate the detoxification pathway using tolerant corn and soybean seedlings. Acetochlor is rapidly absorbed and metabolized by etiolated corn seedlings to the glutathione conjugate and is also rapidly metabolized by etiolated soybean seedlings. However, the initial metabolite by soybean seedlings is the homoglutathione conjugate, not the glutathione conjugate.

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

Synthetic route

C12H19NO + chloroacetyl chloride (79-04-9) → Acetochlor (34256-82-1)

Conditions	Yield
In Petroleum ether for 5h; Reflux; Green chemistry; Industrial scale;	91%

N-(2-methyl-6-ethyl)-phenyl-N-ethyloxymethyl-carbamoyl chloride (56917-59-0) + chloroacetic acid (79-11-8) → Acetochlor (34256-82-1)

Conditions	Yield
In water; benzene	82%

2-chloro-2'-ethyl-6'-methylacetanilide (32428-71-0) + ethyl chloromethyl ether (3188-13-4) → Acetochlor (34256-82-1)

Conditions	Yield
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) → Acetochlor (34256-82-1)

Conditions	Yield
With hydrogen; triethylamine; palladium on activated charcoal In ethanol for 3h; Ambient temperature;	14 mg

pyridine (110-86-1) + Acetochlor (34256-82-1) → N'-pyridinium chloride

piperidine (110-89-4) + Acetochlor (34256-82-1) → N-ethoxymethyl-N-(piperidinylacetyl)-2-ethyl-6-methylbenzeneamine

Conditions	Yield
In ethanol for 3h; Substitution; Heating;

3,4-dichlorothiophenol (5858-17-3) + Acetochlor (34256-82-1) → 2-(3,4-dichloro-phenylsulfanyl)-N-ethoxymethyl-N-(2-ethyl-6-methyl-phenyl)-acetamide

Conditions	Yield
With sodium carbonate In ethanol; water for 0.5h; Substitution; Heating;

Acetochlor (34256-82-1) + 2,3,6-trimethyl-beta-cyclodextrin (55216-11-0) → C63H112O35*C14H20ClNO2 (1448818-09-4)

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

Upstream product

• 32428-71-0 2-chloro-2'-ethyl-6'-methylacetanilide 
• 3188-13-4 ethyl chloromethyl ether 
• 56917-59-0 N-(2-methyl-6-ethyl)-phenyl-N-ethyloxymethyl-carbamoyl chloride 
• 79-11-8 chloroacetic acid 
• 79-04-9 chloroacetyl chloride 
• 161499-20-3 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-4-iodo-6-methylphenyl)acetamide 

Downstream Products

• 1448818-09-4 C₆₃H₁₁₂O₃₅*C₁₄H₂₀ClNO₂ 

Relevant articles and documents

Synthesizing method for chloroacetamide compound

The invention discloses a synthesizing method for a chloroacetamide compound. In a reaction kettle, a secondary amine compound is dissolved in an organic solvent, the mixture is heated for reflux, chloroacetyl chloride is added into the mixture, a reflux reaction is conducted for 0.5-20 hours, and the chloroacetamide compound is obtained. According to the synthesizing method for the chloroacetamide compound, an acid binding agent is not used, discharging of wastewater in the after-treatment process is reduced, by keeping the reflux state of the system, hydrogen chloride gas generated from thereaction is exhausted out of the system and absorbed by water outside the system, high-purity hydrochloric acid is obtained, the waste is turned into wealth, the method comes up to the production standard of safety and environment protection, and discharging of waste gas, waste water and waste residues is reduced; according to the synthesizing method for the chloroacetamide compound, few operationsteps are utilized, the reaction speed is high, the product yield is high, the purity is high, the production cost is low, and the method is safe, friendly to the environment and suitable for industrial large-scale production.

Herbicidal mixtures having a synergistic effect

PCT No. PCT/EP96/03996 Sec. 371 Date Feb. 17, 1998 Sec. 102(e) Date Feb. 17, 1998 PCT Filed Sep. 12, 1996 PCT Pub. No. WO97/10714 PCT Pub. Date Mar. 27, 1997A composition comprising at least one sulfonylurea of the formula I wherein R1 is substituted alkyl; halogen; a group ER6 (E=O, S or NR7); COOR8; NO2; S(O)oR9; SO2NR10R11; or CONR10R11; R2 is hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkoxy, haloalkyl, alkylsulfonyl, nitro, cyano or alkylthio; R3 is F, CF3, CF2Cl, CF2H, OCF3, OCF2Cl, or, if R1 is CO2CH3 and R2 is simultaneously fluorine, R3 is Cl, or, if R1 is CH2CF3 or CF2CF3, R3 is methyl, or, if R4 is OCF3 or OCF2Cl, R3 is OCF2H or OCF2Br; R4 is alkoxy, alkyl, alkylthio, alkylamino, dialkylamino, halogen, haloalkyl or haloalkoxy; and R5 is hydrogen, alkoxy or alkyl; or an enviromentally compatible salt of I, and an aryloxyalkanoic acid selected from the group consisting of 2,4-D, 2,4-DB, clomeprop, dichlorprop, dichlorprop-P, dichlorprop-P (2,4-DP-P), fenoprop (2,4,5-TP), fluoroxypyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napropanilide, triclopyr, and an enviromentally compatible salt thereof exhibits a synergistic herbicidal effect.

Radiosynthesis of a Chloroacetanilide Herbicide (Acetochlor) and a Dichloroacetamide Safener for Herbicides (R-29148)

2-Chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide (the chloroacetanilide herbicide acetochlor) and 3-(dichloroacetyl)-2,2,5-trimethyl-1,3-oxazolidine (the dichloroacetamide safener R-29148) are required at high specific activity for studies on their metabolism and mode of action. Acetochlor was obtained at 22 Ci/mmol in 71percent yield by reductive dehalogenation of iodoacetochlor with tritium gas in ethanol in the presence of palladium on carbon and triethylamine. R-29148 was prepared at 15 Ci/mmol by treating acetone and 1-amino-2-propanol in pentane with two equivalents of NaOH in tritiated water (i.e. hydroxide ion-catalyzed enolization of acetone) followed by dichloroacetyl chloride.Key words: acetochlor, chloroacetanilide, deuterium labeling, dichloroacetamide, herbicides, R-29148, safeners, tritiated water, tritium gas, tritium labeling