34256-82-1

Usage

Uses

Used in Agriculture:
Acetochlor is used as a herbicide for controlling grasses and broadleaf weeds in crops such as corn, soybeans, sorghum, and peanuts that are grown in high organic content soil. Its application helps to improve crop yield by reducing competition from weeds and ensuring that the nutrients are directed towards the growth of the desired crops.

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

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

Downstream Products

• 1448818-09-4 C₆₃H₁₁₂O₃₅*C₁₄H₂₀ClNO₂ 

Relevant academic research and scientific papers

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.

NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND

An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.

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.

Herbicidal compositions comprising diamino-1,3,5-triazine and chloroacetanilide herbicides and a surfactant system

Flowable herbicidal compositions which contain an active component combination of at least one triazine and at least one chloroacetanilide with a surfactant component. This surfactant component, which consists of an anionic compound based on a monosulfuric acid ester of alkyl or alkyphenol polyglycol ethers as well as at least one nonionic alkyl or alkylphenol polyglycol ether, gives stable dispersions of the concentrated composition and forms stable dispersions of dilutions of the compositions suitable for direct use.

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

Sulfamoylphenylureas

The N-acylsulfamoylphenylureas of formula I below are suitable as counter-agents (antidotes or safeners) for protecting cultivated plants from the phytotoxic action of herbicides. Suitable crops are preferably cereals, soybeans, sorghum, maize and rice, and suitable herbicides are sulfonylureas, chloroacetanilides and aryloxyphenoxypropionic acid derivatives. The N-acylsulfamoylphenylureas have the formula I STR1 wherein A is a radical selected from the group STR2 R1 is C1 -C4 -alkoxy or each of R1 and R2, independently of the other, is hydrogen, C1 -C8 alkyl, C3 -C8 cycloalkyl, C3 -C6 alkenyl, C3 -C6 alkynyl, STR3 or C1 -C4 alkyl substituted by C1 -C4 alkoxy or by STR4 or R1 and R2 together form a C4 -C6 alkylene bridge, or a C4 -C6 alkylene bridge interrupted by oxygen, sulfur, SO, SO2, NH or by --N(C1 -C4 alkyl)-, R3 is hydrogen or C1 -C4 alkyl, Ra to Rh, Rx and Ry are as defined in the disclosure.

Safening mixtures of sulfonylurea and acetanilide herbicides

The disclosure herein relates to safening crops from injury by herbicidal mixtures of sulfonylurea and acetanilide herbicides by means of 5-heterocyclyl-substituted dichloroacetamide antidotes.

N-phenylpyrrolidines

The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives of the formula I below are suitable for protecting crop plants against the phytotoxic action of herbicides and for regulating the plant growth. The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives are those of the formula I STR1 wherein A is --COOR1, --COSR1, --COO? M≈, --CONR2 R3 or --COCl; R1 is hydrogen, C1 -C4 alkyl, C2 -C6 alkenyl or C2 -C6 alkynyl; R2 and R3 independently of one another are hydrogen, C1 -C4 alkyl or C3 -C7 cycloalkyl; or R2 and R3 together with the nitrogen atom to which they are bonded are a saturated 3- to 7-membered heterocycle which can contain an additional hetero atom selected from the group comprising O, N and S and which is unsubstituted or up to trisubstituted by C1 14 C4 alkyl; and M≈ is the equivalent of an alkali metal cation or an alkaline earth metal cation or HN≈ (R2)3, and their isomers in optically pure or enriched form.

Safening herbicidal benzoic acid derivatives

The disclosure herein relates to the use of certain amdies of dichloroacetic acid and other compounds as safener/antidotal compounds to reduce the phytotoxicity to crop plants, especially corn, of benzoic acid-type herbicides alone or in admixture with other co-herbicidal compounds, e.g., α-haloacetamides.

Benzhydryl compounds as herbicide antidotes

Acids, esters, amides and salts of benzhydryl compounds are antidotes for thiocarbamate and acetamide herbicides. These antidote compounds are especially effective to safen acetamide herbicides used to control grassy weeds and broadleaf weeds in rice, sorghum, corn and wheat.