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Metolachlor Basic information
Metolachlor Chemical Properties
Safety Information
Metolachlor Usage And Synthesis
  • Chemical PropertiesPale Yellow Oil
  • Chemical PropertiesMetolachlor is a colorless or tan to brown, oily liquid. Slightly sweet odor.
  • UsesPreemergence 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.
  • UsesA selective pre-emergence herbicide.
  • General DescriptionTan 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 ReactionsSlightly soluble in water. Hydrolyzed by strong mineral acids and strong alkalis.
  • Reactivity ProfileMetolachlor 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 HazardCan cause skin irritation and eye irritation. Headache and nausea may occur following prolong exposure.
  • Agricultural UsesHerbicide: 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.
  • Potential ExposureMetolachlor 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 FateSoil. 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 pathwayA 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.
  • ShippingUN2902 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.
  • IncompatibilitiesIncompatible 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).
  • Waste DisposalIn accordance with 40CFR 165 recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
Metolachlor Preparation Products And Raw materials
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