67129-08-2

Basic information

• Product Name: Metazachlor
• Synonyms: BUTISAN S;METAZACHLOR;2-CHLORO-N-(2,6-DIMETHYLPHENYL)-N-(PYRAZOL-1-YLMETHYL)ETHANAMIDE;2-chloro-n-(2,6-dimethylphenyl)-n-(1h-pyrazol-1-ylmethyl)acetamide;2-CHLORO-N-(2,6-DIMETHYLPHENYL)-N-(1-PYRAZOLYLMETHYL) ACETAMIDE;2-chloro-n-(2,6-dimethylphenyl)-n-(1h-pyrazol-1-ylmethyl)-acetamid;2-Chloro-N-(pyrazol-1-ylmethyl)acet-2',6'-xylidide;BAS 47900H
• CAS NO: 67129-08-2
• Molecular Formula: C₁₄H₁₆ClN₃O
• Molecular Weight: 277.75
• EINECS: 266-583-0
• Product Categories: META - METHPesticides&Metabolites;Alpha sort;AmidePesticides&Metabolites;Herbicides;H-MAlphabetic;M;Pesticides&Metabolites;Pyrazole;Agro-Products;Aromatics;Heterocycles;MTS & Sulfhydryl Active Reagents
• Mol File: 67129-08-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 74-78°C
• Boiling Point: 439.2 °C at 760 mmHg
• Flash Point: 2 °C
• Appearance: /
• Density: 1.19 g/cm³
• Vapor Pressure: 6.5E-08mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: APPROX 4°C
• Solubility: Chloroform, Methanol
• PKA: 1.54±0.10(Predicted)
• BRN: 621550
• CAS DataBase Reference: Metazachlor(CAS DataBase Reference)
• NIST Chemistry Reference: Metazachlor(67129-08-2)
• EPA Substance Registry System: Metazachlor(67129-08-2)

Safety Data

• Hazard Codes: Xn,F
• Statements: 22-36-20/21/22-11-43
• Safety Statements: 36-26-16-36/37
• RIDADR: UN 1648 3/PG 2
• WGK Germany: 3
• RTECS: AB5442000
• Hazardous Substances Data: 67129-08-2(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Solid

Uses

A chloroacetanilide herbicide used on vegetable crops.

Definition

ChEBI: An organochlorine compound that is 2-chloroacetamide substituted by a 2,6-dimethylphenyl and a (1H-pyrazol-1-ylmethyl) group at the nitrogen atom.

Metabolic pathway

Metazachlor is transformed in soil into 2-hydroxy-N- (2,6-dimethylphenyl)-N-(1H-pyrazol-1- ylmethyl)acetamide, 2-chloro-N-(2,6- dimethylphenyl)acetamide, and 4,4' -methylenebis-(2,6- dimethylbenzenamine), and the soil concentration of the benzenamine is lower than 0.1 ppm.

InChI:InChI=1/C14H16ClN3O/c1-11-5-3-6-12(2)14(11)18(13(19)9-15)10-17-8-4-7-16-17/h3-8H,9-10H2,1-2H3

Synthetic route

1-(N-2,6-dimethylaniline)-1-(1N-pyrazol)-methane (125709-82-2) + chloroacetyl chloride (79-04-9) → Metazachlor (67129-08-2)

Conditions	Yield
In cyclohexane for 6h; Reflux; Green chemistry; Industrial scale;	95%

NH-pyrazole (288-13-1) + N-(chloromethyl)-N-(2,6-dimethylphenyl)-α-chloroacetamide (61706-54-5) → Metazachlor (67129-08-2)

Conditions	Yield
In toluene at 74℃; under 217.522 Torr; for 12h; Temperature; Time; Pressure; Concentration;

Metazachlor (67129-08-2) → N-((1H-pyrazol-1-yl)methyl)-N-(2,6-dimethylphenyl)acetamide

Conditions	Yield
With hydrogen; triethylamine In methanol; water at 120℃; under 22502.3 Torr; for 44h; Autoclave;	93%
With hydrogen; triethylamine In ethanol; water at 120℃; under 22502.3 - 37503.8 Torr; for 44h; Autoclave;	93%

Metazachlor (67129-08-2) → 2-hydroxy-N-(2,6-dimethylphenyl)-N-(1H-pyrazol-1-ylmethyl)-acetamide (125709-81-1)

Conditions	Yield
potassium hydroxide In water for 4h; Product distribution; Mechanism; Heating; variation of catalyst concentration, reaction time;	75%
potassium hydroxide In water for 4h; Heating;	75%

Metazachlor (67129-08-2) → NH-pyrazole (288-13-1) + 4,4'-methylenebis(2,6-dimethylaniline) (4073-98-7)

Conditions	Yield
hydrogenchloride In water for 8h; Heating;	A 59% B 35%

Metazachlor (67129-08-2) → NH-pyrazole (288-13-1) + 4,4'-methylenebis(2,6-dimethylaniline) (4073-98-7) + 2-chloro-N-(2,6-dimethylphenyl)acetamide (1131-01-7)

Conditions	Yield
hydrogenchloride In water for 5h; Product distribution; Mechanism; Heating; variation of catalyst concentration, reaction time;	A 47% B 21% C 12%

Metazachlor (67129-08-2) → NH-pyrazole (288-13-1) + 2-chloro-N-(2,6-dimethylphenyl)acetamide (1131-01-7)

Conditions	Yield
hydrogenchloride In water for 2h; Heating;	A 40% B 42%

Metazachlor (67129-08-2) → 4,4'-methylenebis-(N-acetyl-2,6-dimethylbenzenamine) (125709-83-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 35 percent / 2.56 N hydrochloric acid / H2O / 8 h / Heating 2: 85 percent / benzene / 2 h / Heating View Scheme

malonic acid (141-82-2) + Metazachlor (67129-08-2) → metazachlor malonic acid

Conditions	Yield
In tetrahydrofuran at 20℃;

oxalic acid (144-62-7) + Metazachlor (67129-08-2) → metazachlor oxalic acid

Conditions	Yield
In tetrahydrofuran at 20℃;

Metazachlor (67129-08-2) + benzoic acid (65-85-0) → metazachlor benzoic acid

Conditions	Yield
In acetone at 20℃;

(2E)-but-2-enedioic acid (110-17-8) + Metazachlor (67129-08-2) → metazachlor fumaric acid

Conditions	Yield
In tetrahydrofuran at 50℃;

3,5-Dihydroxybenzoic acid (99-10-5) + Metazachlor (67129-08-2) → metazachlor 3,5-dihydroxybenzoic acid

Conditions	Yield
In tetrahydrofuran at 400℃; for 0.5h;

Upstream product

• 288-13-1 NH-pyrazole 
• 61706-54-5 N-(chloromethyl)-N-(2,6-dimethylphenyl)-α-chloroacetamide 
• 125709-82-2 1-(N-2,6-dimethylaniline)-1-(1N-pyrazol)-methane 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 75972-11-1 N-((1H-pyrazol-1-yl)methyl)-N-(2,6-dimethylphenyl)acetamide 
• 125709-81-1 2-hydroxy-N-(2,6-dimethylphenyl)-N-(1H-pyrazol-1-ylmethyl)-acetamide 
• 288-13-1 NH-pyrazole 
• 4073-98-7 4,4'-methylenebis(2,6-dimethylaniline) 
• 1131-01-7 2-chloro-N-(2,6-dimethylphenyl)acetamide 
• 125709-83-3 4,4'-methylenebis-(N-acetyl-2,6-dimethylbenzenamine) 

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.

PROCESS FOR PREPARING ACETANILIDES

The present invention relates to a novel process for preparing acetanilides of the formula (I) by reacting a 2-halo-N-halomethylacetanilide of the formula (II) with an azole of the formula (III) H-A (III) wherein the substituents R, R1, R 2, R 3, R 4, A, X and X1 in the formulae (I), (II) and (III) have the meanings as indicated in the description.

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.