METOLCARB

Description

Metolcarb (17), m-tolyl methylcarbamate (IUPAC), C9H11NO2, MW 165.2, mp 76–77 ?C, is a colorless solid that is moderately soluble in water and is readily soluble in polar organic solvents.

Chemical Properties

Metolcarb is a colorless crystalline solid.

Uses

Metolcarb is used to control planthoppers, leafhoppers and other sucking pests on rice. It is also used for control of citrus mealybugs, onion thrips, Mediterranean fruit flies, pink bollworms and cotton aphids.

Preparation

Metolcarb is produced by the reaction between 3- methylphenol and Metolcarb.

Definition

ChEBI: Metolcarb is a carbamate ester. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a carbamate insecticide, an acaricide and an agrochemical. It is functionally related to a methylcarbamic acid and a m-cresol.

General Description

Colorless crystalline solid. METOLCARB is an insecticide for the control of rice leafhoppers, planthoppers, codling moth, citrus mealybug, onion thrips, fruit flies, bollworms and aphids. Not registered as a pesticide in the U.S.

Air & Water Reactions

Soluble in water.

Reactivity Profile

METOLCARB is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

Health Hazard

High oral and skin toxicity, and moderate inhalation toxicity. (Non-Specific -- Carbamates) Some carbamates appear to be carcinogenic, teratogenic, and/or mutagenic. Carbamates are cholinesterase inhibitors.

Health Hazard

Highly toxic by ingestion and moderately toxic by inhalation and skin absorption; cholinesterase inhibitor; exhibits acute,delayed, and chronic toxicity; toxic effects arethose of organophosphorus pesticides and carbamate esters; the symptoms include excessive salivation, lacrimation, blurred vision,headache, labored breathing, twitches ofmuscle, loss of reflexes, headache, weakness, sweating, nausea, giddiness, vomiting,cramps, diarrhea, convulsions, and coma; U.S.EPA-listed extremely hazardous substance.
LD50 oral (rat): 268 mg/kg
LD50 skin (rat): 268 mg/kg
LD50 inhalation (rat): 128 mg/m³ hour.

Fire Hazard

As for other solid carbamate pesticides, container may explode in heat of fire. Fire and runoff from fire control water may produce irritating or poisonous gases. Emits toxic fumes of nitrogen oxides when heated to decomposition. Avoid decomposing heat.

Agricultural Uses

Insecticide, Acaricide: Metolcarb is an insecticide for the control of rice green leafhoppers, plant-hoppers, codling moth, citrus mealy bug, onion thrips, fruit flies, bollworms and aphids. Not registered for use in the U.S. Not listed for use in EU countries.

Trade name

DRC 3341®; KUMIAI®; METACRATE®; S 1065®; SOGATOX DUST® 22; TSUMACIDE®; TSUMAUNKA®; VADEN®

Safety Profile

Poison by ingestion and skin contact. Moderately toxic by inhalation. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also CARBAMATES.

Potential Exposure

Metolcarb is an insecticide used for the control of rice leafhoppers, plant-hoppers; codling moth; citrus mealy bug; onion thrips; fruit flies; bollworms and aphids. Not registered as a pesticide in the United States.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Speed in removing material from skinis of extreme importance. Shampoo hair promptly if contaminated. Seek medical attention immediately. If thischemical has been inhaled, remove from exposure, beginrescue breathing (using universal precautions, includingresuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit. Keepvictim quiet and maintain normal body temperature.Carefully observe victim since effects may be delayed.

Metabolic pathway

The main pathways of metabolism of metolcarb in plants, mammals and insects involve ring-methyl, N-methyl and phenyl-ring hydroxylation and conjugation. Carbamate ester hydrolysis is a minor reaction. Further oxidation of a ring-hydroxymethyl moiety to carboxyl occurs in rats and insects.

storage

Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, wellventilated area away from oxidizers. Where possible, automatically pump liquid from drums or other storage containers to process containers

Shipping

UN2757 Carbamate pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Incompatibilities

Carbamates are incompatible with reducing agents such as hydrides, strong acids, oxidizing acids, peroxides, and bases. Contact with active metals or nitrides cause the release of flammable, and potentially explosive, hydrogen gas. May react violently with bromine, ketones. Incompatible with azo dyes, caustics, ammonia, amines, boranes, hydrazines, strong oxidizers.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal. In accordance with 40CFR165, follow 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.