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
• Article Data: 16

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

Chemical Properties

Different sources of media describe the Chemical Properties of 51218-45-2 differently. You can refer to the following data:
1. Pale Yellow Oil
2. Metolachlor is a colorless or tan to brown, oily liquid. Slightly sweet odor.

Uses

Different sources of media describe the Uses of 51218-45-2 differently. You can refer to the following data:
1. Preemergence herbicide used to control most annual grasses and many annual weeds in beans, chickpeas, corn, cotton, milo, okra, peanuts, peas, potatoes, safflower, soybeans and some ornamentals.
2. A selective pre-emergence herbicide.

General Description

Tan to brown oily liquid with a slightly sweet odor. Slightly soluble in water and denser than water. Hence sinks in water. Soluble in most organic solvents. Used as a selective herbicide.

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.

Agricultural Uses

Herbicide: Not approved for use in EU countries. Registered for use in the U.S. Metolachlor is a selective herbicide that is usually applied to crops before plants emerge from the soil, and is used to control 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. Prior to the RED of April, 1995, its primary use was on corn, soybeans and sorghum. It inhibits protein synthesis; thus, high-protein crops (e. g., soy) can be adversely affected by excessive metolachlor application. Additives may be included in product formulations to help protect sensitive crops (i.e., sorghum) from injury.

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

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

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 
• 65513-61-3 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-hydroxy-1-methylethyl)acetamide 
• 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 
• 171118-09-5 2-[(2-ethyl-6-methylphenyl)(2-methoxy-1-methylethyl)amino]-2-oxoethanesulfonic acid 
• 65513-63-5 8-ethyl-3-hydroxy-N-(2-methoxy-1-methylethyl)-2-oxo-1,2,3,4-tetrahydroquinolinen 
• 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 

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.

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.