51218-45-2

Basic information

• Product Name: Metolachlor
• Synonyms: 2-aethyl-6-methyl-n-(1-methyl-2-methoxyaethyl)-chloracetanilid;2-chloro-2’-ethyl-n-(2-methoxy-1-methylethyl)-6’-methylacetanilide;2-chloro-6’-ethyl-n-(2-methoxy-1-methylethyl)-o-acetotoluidid;2-chloro-6’-ethyl-n-(2-methoxy-1-methylethyl)-o-acetotoluidine;2-chloro-n-(6-ethyl-o-tolyl)-n-(2-methoxy-1-methylethyl)-acetamid;2-ethyl-6-methyl-1-n-(2-methoxy-1-methylethyl)chloroacetanilide;2-etylo-6-metylo-n-(1’-metylo-2’-metoksyetylo)chloroacetanilid;Acetamide, 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)-
• CAS NO: 51218-45-2
• Molecular Formula: C₁₅H₂₂ClNO₂
• Molecular Weight: 283.79
• EINECS: 257-060-8
• Product Categories: Agro-Chemicals;HERBICIDE;Alpha sort;AmideMethod Specific;Endocrine Disruptors (Draft)Pesticides&Metabolites;EPA;Herbicides;H-MAlphabetic;M;METI - MZ;Pesticides&Metabolites;Amines;Aromatics
• Mol File: 51218-45-2.mol

Chemical Properties

• Melting Point: 25°C
• Boiling Point: bp0.001 100°
• Flash Point: 2 °C
• Appearance: Tan to brown oily liquid with a slightly sweet odor
• Density: 1.1200
• Vapor Pressure: 7.91E-07mmHg at 25°C
• Refractive Index: 1.526-1.529
• Storage Temp.: APPROX 4°C
• PKA: 1.45±0.50(Predicted)
• Water Solubility: 529.7mg/L(20 oC)
• BRN: 8396147
• CAS DataBase Reference: Metolachlor(CAS DataBase Reference)
• NIST Chemistry Reference: Metolachlor(51218-45-2)
• EPA Substance Registry System: Metolachlor(51218-45-2)

Safety Data

• Hazard Codes: Xi,Xn,F
• Statements: 43-36-20/21/22-11
• Safety Statements: 36/37-36-26-16
• RIDADR: UN1648 3/PG 2
• WGK Germany: 2
• RTECS: AN3430000
• Hazardous Substances Data: 51218-45-2(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
Metolachlor is used as a pre-emergence herbicide for controlling most annual grasses and many annual weeds in various crops such as beans, chickpeas, corn, cotton, milo, okra, peanuts, peas, potatoes, safflower, soybeans, and some ornamentals.
Metolachlor is also used as a selective pre-emergence herbicide in the U.S. for controlling certain broadleaf and annual grassy weeds in field corn, soybeans, peanuts, grain sorghum, potatoes, pod crops, cotton, safflower, stone fruits, nut trees, highway rights-of-way, and woody ornamentals. It is not approved for use in EU countries. Metolachlor works by inhibiting protein synthesis, which can adversely affect high-protein crops like soybeans if applied excessively. Additives may be included in product formulations to protect sensitive crops like sorghum from potential injury.

Air & Water Reactions

Slightly soluble in water. Hydrolyzed by strong mineral acids and strong alkalis.

Reactivity Profile

Metolachlor is a chlorinated acetamide. May react with azo and diazo compounds to generate toxic gases. May form flammable gases with strong reducing agents. Combustion generates mixed oxides of nitrogen (NOx).

Health Hazard

Can cause skin irritation and eye irritation. Headache and nausea may occur following prolong exposure.

Trade name

BICEP?[C]; BROADSTRIKE?; CGA- 24705?; CINCH?; CODAL?; COTORAN? MULTI?; CYCLE?[C] DREXEL ME-TOO-LACHLOR?; DUAL?; DUAL MAGNUM?; DUET?[C]; INTER PLUS?; MEDAL?[C]; MILOCEP?; ONTRACK 8E?[C]; PENNANT?[C]; PRELUDE?[C]; PRIMAGRAM?; PRIMEXTRA?; TURBO?

Potential Exposure

Metolachlor is a chlorinated acetamide selective herbicide used for weed control in corn and for controlling grasses in a variety of crops including cotton and peanuts.

Environmental Fate

Soil. Metolachlor and its degradation products combine with humic acids in soils and small quantities are degraded to carbon dioxide (Ashton and Monaco, 1991). In soil, the fungus Chaetomium globosum degraded metolachlor to 2-chloro-N-(2-ethyl-6-methylphenyl) acetamide, 2-hydroxy-N-(2-methylvinylphenyl)-N-(methoxyprop-2-yl)acetamide, 3- hydroxy-8-methyl-N-(methoxyprop-2-yl)-2-oxo-1,2,3,4-tetrahydraquinoline, 2-chloro-N- (2-ethyl-6-methylphenyl)-N-(hydroxyprop-2-yl)acetamide and the tentatively identified compounds 3-hydroxy-1-isopropyl-8-methyl-2-oxo-1,2,3,4-tetrahydroquinoline, N-(methoxyprop- 2-yl)-8-methyl-2-oxo-1,2,3,4-tetrahydroquinoline, N-(methoxyprop-2-yl)-N-(2- methyl-6-vinyl)aniline and 1-(methoxyprop-2-yl)-7-methyl-2,3-dihydroindole (McGahen 8). Metolachlor was transformed by a strain of soil actinomycetes to the following products: 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(hydroxyprop-2-yl)acetamide, 2-chloro-N- 2-(1-hydroxyethyl)-6-(methylphenyl)-N-(hydroxyprop-2-yl)acetamide, 2-chloro-N-(2- ethyl-6-hydroxymethylphenyl)-N-(hydroxy-prop-2-yl)-acetamide, diastereoisomers of 2- chloro-N-(2-ethyl-6-hydroxymethylphenyl)-N-(methoxyprop-2-yl)acetamide and 2- chloro-N-2-(hydroxyethyl)-6-hydroxymethylphenyl)-N-(methoxyprop-2-yl)acetamide. These products were formed via hydroxylation of both the N-alkyl and alkyl side chains (Krause et al., 1985). In sterilized soil, metolachlor did not degrade after 4 months (Bouchard et al., 1982). Zimdahl and Clark (1982) reported half-lives of 15–38 and 33–100 days for the herbicide in clay loam soil and sandy loam soil, respectively. They also reported that soil moisture increased the dissipation rate. At 20°C, the dissipation rates of metolachlor in the clay loam and sandy loam soils at 20, 50 and 80% soil moisture contents were 0.028, 0.053, 0.062 and 0.016, 0.028 and 0.037/day, respectively. The half-lives of metolachlor in soil at maintained at temperatures of 30 and 40°C were approximately 3.85 and 2.75 weeks, respectively (Bravermann et al., 1986). The reported half-lives of metolachlor in soil is approximately 6 days (Worthing and Hance, 1991) and 3–4 weeks (Bowman, 1988). Groundwater. According to the U.S. EPA (1986) metolachlor has a high potential to leach to groundwater. Plant. Metabolizes in plants forming water soluble, polar, nonvolatile products (Hartley and Kidd, 1987) and glutathione conjugates (Breaux et al., 1987). Chemical/Physical. The volatilization half-life of metolachlor in an unstirred solution was 20 days at 40°C. Volatilization is not significant at temperatures < 25°C (Lau et al., 1995).

Metabolic pathway

A stable bacterial community absorbs and transforms metolachlor from a liquid medium. From the medium of the 7 day-old culture of the bacterial community, 2- hydroxy-N-(2-methyl-6-vinylphenyl)-N-(2-methoxy- methylethyl)acetamide and 4-(2-ethyl-6-methylphenyl)- 5-methyl-3-morpholinone are identified. The products recovered from cells of J4-A include dechlorinated metolachlor, a thiol compound, a more complicated conjugate, and a non-sulfur-containing conjugate. By sorghum microsomes, O-demethylation occurs in the metolachlor degradation process.

Shipping

UN2902 Pesticides, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, nitrates. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur).

InChI:InChI=1/C15H22ClNO2/c1-5-13-8-6-7-11(2)15(13)17(14(18)9-16)12(3)10-19-4/h6-8,12H,5,9-10H2,1-4H3

Upstream product

• 51219-00-2 2-methyl-6-ethyl-N-(1-methyl-2-methoxyethyl)aniline 
• 79-04-9 chloroacetyl chloride 
• 118604-68-5 N-(2’-methyl-6’-ethyl-phenyl)-N-1-(methoxymethyl)ethylimine 
• 24549-06-2 6-ethyl-o-toluidine 

Downstream Products

• 68545-40-4 N-(2-Ethyl-6-methyl-phenyl)-N-(2-methoxy-1-methyl-ethyl)-2-methylsulfanyl-acetamide 
• 126605-22-9 N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide 
• 65513-63-5 8-ethyl-3-hydroxy-N-(2-methoxy-1-methylethyl)-2-oxo-1,2,3,4-tetrahydroquinolinen 
• 120375-14-6 4-(2-ethyl-6-methylphenyl)-5-methyl-3-morpholinone 
• 131068-72-9 2-hydroxy-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide 
• 96394-95-5 2-chloro-N-[2-(1-hydroxyethyl)-6-methylphenyl]-N-(2-hydroxy-1-methylethyl)acetamide 
• 96411-89-1 2-chloro-N-(2-ethyl-6-hydroxymethylphenyl)-N-(2-hydroxy-1-methylethyl)acetamide 
• 65513-61-3 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-hydroxy-1-methylethyl)acetamide 
• 171118-09-5 2-[(2-ethyl-6-methylphenyl)(2-methoxy-1-methylethyl)amino]-2-oxoethanesulfonic acid 

Relevant articles and documents

Compound herbicide based on dichloro quinolinic acid

The invention discloses a compound herbicide based on quinclorac, which comprises 20 - 30 parts of quinclorac. Dichloromethane 3-8 parts, synergist 10 - 20 parts, wetting agent 1.5 - 4.5 parts, dispersing agent 1-3 parts, defoaming agent 0.5 - 2.5 parts and water 50 - 70 parts. The synergist inhibits the growth of cells by hindering the synthesis of the protein, and the sprouts of monocotyledonous plants are obtained through young buds of plants. The lower endoderm of the dicotyledonous plant is absorbed and conducted upwards, the seeds and roots absorb conduction, the absorption amount is low, the conduction speed is slow, the growth of young buds and roots is inhibited.

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.

Synthesis method of metolachlor

A synthesis method of metolachlor comprises the steps of: (1) hydrogenation alkylation: dissolving2-methyl-6-ethyl aniline and methoxy acetone with an organic solvent A, adding a hydrogenation catalyst, introducing hydrogen to conduct a hydrogenation alkylation reaction, and concentrating the solvent after the reaction to obtain a reaction product B, wherein the hydrogenation catalyst is a composition of palladium carbon, Raney nickel and phosphoric acid in the weight ratio of 1-2:4-10:2-5, and the temperature of the hydrogenation alkylation reaction is 30-90 DEG C; and (2) acylation: conducting an acylation reaction on the product B with chloroacetyl chloride under the catalysis of an acid-binding agent, and conducting post-treatment after the reaction to obtain refined metolachlor. The synthesis method of metolachlor provided by the present invention has the advantages of simple operation, short production cycle, small amount of organic reagent and emission, high yield and purity of the desired products, no additional solvent in the post-treatment process, reduction of "three wastes" emissions; and the production process is safe, environmentally friendly and applicable to mass industrial 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.

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.

Halopyridyl triazolinone herbicides and herbicidal use thereof

Disclosed are herbicidal halopyridyl triazolinones, herbicidal compositions comprising the halopyridyl triazolinones, and herbicidal use of the compounds and compositions. Such compounds and compositions are useful as both preemergence and postemergence herbicides in a variety of crops.

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.

Leaching inhibition of crop treating chemicals with nitrogen containing polymers

This invention relates to inhibiting leaching of crop treating chemicals into the ground water, aqua-system and surrounding soil of the treatment site by contacting the plant or plant site with an effective leach inhibiting, plant tolerating amount of a nitrogen-containing copolymer having pendant nitrogeneous groups which contains between about 40 and about 98 wt. % of monomer unit A defined by the formula STR1 and 2 to 40 wt. % of comonomer unit B STR2 wherein X is hydrogen, a C1 to C22 radical of the group alkyl, alkoxy, aryl, alkaryl, aryloxy and alkaryloxy; R2 is hydrogen or --(CO)y' OR'; R, R1, R3 and R' are each selected from the group of hydrogen and lower alkyl; R6 is hydrogen or STR3 x, y, y' and z each have a value of 0 or 1; a has a value of from 2 to 4; Z is --O-- or --NH-- Y is an optionally quaternized group of STR4 and R4 and R5 are hydrogen or lower alkyl except that at least one of R4 and R5 is lower alkyl.