Alachlor Chemical Properties

Melting point:

39-42°C

Boiling point:

100°C (0.02 mmHg)

Density 

d2515.6 1.133

refractive index 

1.5388 (estimate)

Flash point:

-18 °C

storage temp. 

2-8°C

solubility 

DMF: 30 mg/ml,DMSO: 30 mg/ml

pka

1.20±0.50(Predicted)

Water Solubility 

0.024 g/100 mL

Merck 

13,201

BRN 

2944476

CAS DataBase Reference

15972-60-8(CAS DataBase Reference)

NIST Chemistry Reference

Alachlor(15972-60-8)

EPA Substance Registry System

Alachlor (15972-60-8)

Safety Information

Hazard Codes 

Xn;N,N,Xn,F,T

Risk Statements 

22-40-43-50/53-67-65-38-11-52/53-39/23/24/25-23/24/25-51/53

Safety Statements 

36/37-46-60-61-62-45-16

RIDADR 

UN 3077

WGK Germany 

3

RTECS 

AE1225000

HazardClass 

9

PackingGroup 

III

Hazardous Substances Data

15972-60-8(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 1200 mg/kg (Evans)

MSDS

• Language:English Provider:2-Chloro-2',6'-diethyl-N-(methoxymethyl)acetanilide

Alachlor Usage And Synthesis

description

Alachlor is a pre- and postemergence herbicide used to control annual grasses and many broad-leaved weeds in corn and in many other crops. There are liquid, dry flowable, microencapsulated, and granular formulations. Alachlor is applied by ground, aerial, and chemigation equipment. It can also be mixed with dry bulk fertilizer. It is lost from soil mainly through volatilization, photodegradation, and biodegradation. Alachlor and its degradation products may be found in soil, groundwater, and surface water.

Chemical Properties

Alachlor is a cream-colored or white solid that dissolves readily in acetone, benzene, and ethanol, but dissolves only slightly in water. It resists breakdown by ultraviolet radiation, but reacts with water under strongly acidic or alkaline conditions.

Uses

It can be used as selective herbicide for dryland bud. If a plant bud absorbs the agent, it can inhibit the activity of the protease and hinder protein synthesis, resulting in the death of weeds. It is mainly used for the germination of weeds in the soil before the seedlings, which is basically ineffective for the unearthed weeds. It can prevent annual grasses in the fields of dryland crops such as soybean, cotton, sugar beet, corn, peanut and rape, such as barnyard grass, Goosegrass, autumn grass, crabgrass, Goosegrass, Setaria, Brachiaria etc.

Toxicity

Alachlor is slightly to practically nontoxic to birds, mammals, and honey bees; highly to moderately toxic to freshwater fish; and highly toxic to aquatic plants.
The acute oral LD50 for rats is 1200mg/kg. The acute percutaneous LD50 for rabbits is 5000mg/kg (13300mg/kg). Acute inhalation is LC50>1.04mg/L in rats. The non action dose of 90d in rats is 17mg/kg, and the chronic non action dose is 2.5mg/kg. It is of no teratogenicity and mutagenesis. Bronchioloalveolar tumors and liver and lung tumors can be found at 15mg/kg and 240 ~ 260mg/kg doses in mice. For carp it is LC503.72mg/L.

Preparation

Alachlor can be synthesized in the following manner:

Precaution

1. If there is no rain in the half month after the use of Methamide, watering or shallow mixed soil should be carried out to ensure the efficacy. But the accumulation of soil water is easy to take place.
2. Methamide has a certain stimulating effect on the eyes and skin. Care should be paid to the administration and dispensation. If splashed into the eyes and skin, it should be cleaned immediately.
3. Sorghum, millet, cucumber, melon, carrots, spinach, leeks are sensitive to alachlor and it should not be used for these plants.
4. Methamide should be kept at the temperature above 0℃, and the crystallization will appear at less than 0℃. The crystallized Methamide emulsion can be recovered at 15 - 20 ℃, which does not affect the efficacy of the drug. 5. Alachlor emulsion can dissolve poly vinyl chloride, acrylonitrile, butadiene, styrene plastic and other plastic products. Therefore, this kind of material can not be used as a packing container, without corrosion to metal such as aluminum, iron, stainless steel etc.

Description

Alachlor is a herbicide. Occupational contact dermatitis was rarely observed in agricultural workers.

Chemical Properties

Alachlor is a colorless to yellow crystal chemical substance. It is soluble in most organic solvents, but sparingly in water. Alachlor is an RUP, therefore it should be purchased and used only by certified, trained workers and plant protection applicators. The US EPA categorizes it as toxicity class III, meaning slightly toxic. However, alachlor products bear the signal word danger on their labels because of their potential to cause cancer in laboratory animals. Alachlor is an aniline herbicide used to control annual grasses and broadleaf weeds in field corn, soybeans, and peanuts. It is a selective systemic herbicide, absorbed by germinating shoots and roots. It works by interfering with a plant's ability to produce protein and by interfering with root elongation. Alachlor has extensive use as a herbicide in the United States. It is available as granules or emulsifiable concentrate.

Uses

Alachlor is used pre- or early post-emergence to control annual grasses and many broadleaved weeds mainly in maize, but also in cotton, brassicas, oilseed rape, peanuts, radish, soy beans, and sugar-cane.

Uses

Alachlor is one of the most widely used herbicides in the United States and is used as an herbicide for grasses, broadleaf seeds, corn, sorghum, soybeans, peanuts, cotton, vegetables, and forage crops.

Uses

Preemergence, early postemergence or soil-incorporated herbicide used to control most annual grasses and many annual broad-leaved weeds in beans, corn, cotton, milo, peanuts, peas, soybeans, sunflower and certain woody ornamentals.

Definition

ChEBI: An aromatic amide that is N-(2,6-diethylphenyl)acetamide substituted by a methoxymethyl group at at the nitrogen atom while one of the hydrogens of the methyl group has been replaced by a chlorine atom.

General Description

Crystalline solid. Melting point 104-106°F (40-41°C). Used as a herbicide.

Air & Water Reactions

Hydrolyzes under strongly acidic and strongly basic conditions.

Reactivity Profile

A halogenated acetamide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Health Hazard

Alachlor is a slightly toxic herbicide. It causes slight to moderate degrees of skin irritation. While a 90-day study on laboratory rats and dogs given diets containing low to moderate amounts of alachlor (1–100 mg/kg/day) showed no adverse effects, a 1-year study indicated that at a dose above 1 mg/kg/day, alachlor causes damage in the liver, spleen, and kidney.

Agricultural Uses

Herbicide: A pre-emergence herbicide for corn, soybeans, and peanuts, and other field crops. It is a selective systemic herbicide, absorbed by germinating shoots and by roots. It works by interfering with a plant's ability to produce protein and by interfering with root elongation. It is available as granules or emulsifiable concentrate. Alachlor is used in mixed formulations with atrazine, glyphosate, trifluralin, and imaquin. Not approved for use in the EU. A U.S. EPA restricted Use Pesticide (RUP).

Trade name

AGIMIX® Araclor; ALAGAM®; ALAGAN®; ALANEX®; ALAPAZ®, suspended; ALAZINE®; ALATOX 480®; ALCLOR 48 LE®; CHIMICHLOR®; LARIAT®; LASAGRIN®; LASSAGRIN®; LASSO®; LASSO MICRO-TECH®; METACHLOR®; PARTNER® Arachlor; PILLARZO®; SANACHLOR®

Contact allergens

Alachlor is a herbicide. Occupational contact dermatitis was rarely observed in agricultural workers.

Safety Profile

Moderately toxic by ingestion, skin contact, and possibly other routes. Questionable carcinogen with experimental carcinogenic data. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Cland NOx.

Potential Exposure

A chloracetanilide herbicide. In manufacture, formulation and application of this preemergence herbicide, personnel may be exposed. Its major use (99%) is as a preemergence herbicide for field crops (corn, soybeans, and peanuts, etc.).

Environmental Fate

Alachlor dissipates from soil mainly through volatilization, photodegradation, and biodegradation. Many metabolites have been identified; diethylaniline, detected in some soil studies, interacts rapidly with humic substances in the soil. A half-life in soil of 7-38 days has been reported. Under certain conditions, alachlor can leach beyond the root zone and migrate to groundwater.

Metabolic pathway

The metabolism of alachlor using in vitro incubations with microsomal fractions prepared from liver and nasal turbinate tissues of rat and mouse (m1) results in conversion to 3,5-diethylbenzoquinone-4-imine via the key intermediate of 2,6-diethylaniline, the formation of which requires catalysis by microsomal arylamidases. 2,6-Diethylaniline is oxidized to 4-amino- 3,5-diethylphenol resulting in quinone imine by further oxidation. Rat nasal tissue possesses high enzymatic activity which can promote the formation of the reactive quinone imine. A methylsulfide metabolite of alachlor is shown to be a precursor to 2,6- diethylaniline. The deposition of radioactivity in the rat nasal tissue is more pronounced following oral administration of the methylsulfide metabolite of alachlor.
The extent of DNA adduct formation by alachlor and its metabolites is used as a guide to deduce the causal agent(s) in the carcinogenicity of this herbicide. Metabolic studies (m2) indicate that 2-chloro-N- hydroxymethoxymethyl-N-(2,6-diethylphenyl)- acetamide is an intermediate in forming 2-chloro-N- (2,6-diethylphenyl)acetamide and presumably formaldehyde in the mouse liver microsomal mixed- function oxidase system and in yielding O-glucuronide of 2-chloro-N-hydroxymethyl-N-(2,6- diethylphenyl)acetamide in the urine of alachlor-treated mice.
Incubation of alachlor in the presence of glutathione (GSH) with the cytosolic fraction from rat, mouse, and monkey (m3) produces the GSH conjugate of alachlor as the initial metabolite. The conjugation occurs through thiol displacement of the chlorine atom of alachlor and is catalyzed by glutathione S-transferase (GST). Kidney cell-free preparations of rats and monkeys readily degrade the alachlor GSH conjugate through the mercapturic acid pathway to the corresponding cysteinylglycine, cysteine, and N-acetylcysteine conjugates of alachlor.
Upon UV irradiation, 14/13C-alachlor is dechlorinated and forms a number of intermediates that retain the aromatic ring and carbonyl carbons. These compounds include hydroxyalachlor, norchloralachlor, 2' ,6'-diethylacetanilide, 2-hydroxy- 2' ,6' -diethyl-N-methylacetanilide, and a lactam. The fungus transforms 98.6% of 14C-alachlor added to the fermentation broth, and metabolism occurs predominantly by benzylic hydroxylation of one of the arylethyl side chains. Two major metabolites are isomers of 2-chloro-N-(methoxymethyl)-N-[2-ethyl-6-(1- hydroxyethyl)-phenyl]acetamide and 2-chloro-N-(2,6- diethylphenyl)acetamide. The minor metabolite is 2-chloro-N-(methoxymethyl)-N-(2-vinyl-6- ethlyphenyl)acetamide. N-Dealkylation by fungal biotransformation is also observed.

Shipping

UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Toxicity evaluation

Alachlor has a low persistence in soil, with a half-life ofz8 days. The main means of degradation is by soil microbes. It has moderate mobility in sandy and silty soils, and thus can migrate to groundwater. The largest groundwater-testing program for a pesticide, the National Alachlor Well Water Survey, was conducted throughout the last half of the 1980s. More than sixmillion private and domestic wells were tested for the presence of alachlor. Less than 1% of all of the wells had detectable levels of alachlor. In the wells in which the compound was detected, concentrations ranged from 0.1 to 1.0 mg l
^-1, with themajority having concentrations≈0.2mg l
^-1. Alachlor is relatively stable to hydrolysis and photolysis in water, and degradation in water is not considered as an important environmental fate process. Alachlor appears to be persistent under aquifer biological and geochemical conditions. This means that alachlor can appear in groundwater years after use and can migrate with groundwater away from use areas. Alachlor contamination has resulted in loss of untreated groundwater as a source of drinking water in Florida and other states. The bioaccumulation factor in the channel catfish is 5.8 times the ambient water concentration, indicating that alachlor is not expected to accumulate appreciably in aquatic organisms.

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. Corrosive to iron and steel.

Waste Disposal

This compound is hydrolyzed under strongly acid or alkaline conditions, to chloroacetic acid, methanol, formaldehyde and 2,6-diethylanilne. Incineration is recommended as a disposal procedure. Techniques for alachlor removal from potable water have been reviewed by EPA but the data revealed no superior method. Improper disposal of pesticides is a violation of federal law. Dispose In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers.

Alachlor(15972-60-8)Related Product Information

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