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Oxamyl, also known as N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide (IUPAC), is a broad-spectrum systemic insecticide, nematicide, and acaricide. It consists of colorless crystals that are readily soluble in water, methanol, ethanol, acetone, and fairly soluble in toluene. Oxamyl is produced by chlorination of the oxime of methylglycolate, reaction with methanethiol and alkali, and conversion to the carbamate with methyl isocyanate.

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  • 23135-22-0 Structure
  • Basic information

    1. Product Name: Oxamyl
    2. Synonyms: 1-(dimethylcarbamoyl)-n-((methylcarbamoyl)oxy)thio-formidicacimethyles;2-(dimethylamino)-n-(((methylamino)carbonyl)oxy)-2-oxoethanimidothioicacidm;2-(dimethylamino)-n-(((methylamino)carbonyl)oxy)-ethanimidothioicacimethy;2-(dimethylamino)-n-[[(methylamino)-carbonyl]oxy]-2-oxoethanimidothioicacidme;2-Dimethylamino-1-(methylthio)glyoxal O-methylcarbamoylmonoxime;2-dimethylamino-1-(methylthio)glyoxalo-methylcarbamoylmonoxime;Blade;caswellno561a
    3. CAS NO:23135-22-0
    4. Molecular Formula: C7H13N3O3S
    5. Molecular Weight: 219.26
    6. EINECS: 245-445-3
    7. Product Categories: OMore...Close...;Alpha sort;N-PPesticides&Metabolites;NematicidesAnalytical Standards;AcaricidesPesticides;Alphabetic;CarbamatesMethod Specific;Endocrine Disruptors (Draft)Pesticides&Metabolites;EPA;Insecticides;O;Pesticides;Pesticides&Metabolites
    8. Mol File: 23135-22-0.mol
  • Chemical Properties

    1. Melting Point: 100°C
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: White Solid
    5. Density: 0.9700
    6. Vapor Pressure: 5.1×10-5Pa (25 °C)
    7. Refractive Index: 1.6630 (estimate)
    8. Storage Temp.: 0-6°C
    9. Solubility: N/A
    10. PKA: 10.48±0.46(Predicted)
    11. Water Solubility: 28 g/100 mL
    12. BRN: 2212753
    13. CAS DataBase Reference: Oxamyl(CAS DataBase Reference)
    14. NIST Chemistry Reference: Oxamyl(23135-22-0)
    15. EPA Substance Registry System: Oxamyl(23135-22-0)
  • Safety Data

    1. Hazard Codes: T+;N,N,T+
    2. Statements: 21-26/28-51/53
    3. Safety Statements: 36/37-45-61
    4. RIDADR: UN 2811
    5. WGK Germany: 3
    6. RTECS: RP2300000
    7. HazardClass: 6.1(a)
    8. PackingGroup: I
    9. Hazardous Substances Data: 23135-22-0(Hazardous Substances Data)

23135-22-0 Usage

Uses

Used in Agricultural Industry:
Oxamyl is used as an insecticide, nematicide, and acaricide for the treatment and protection of crops from parasites and insects. It exhibits both oral and contact toxicity to control both sucking and chewing insects and mites in a wide variety of row crops, fruits, vegetables, and ornamentals.
Oxamyl is used as a restricted use pesticide on apples, bananas, carrots, celery, citrus, cotton, cucumbers, eggplants, garlic, ginger, muskmelon (including cantaloupe and honeydew melon), onion (dry bulb), peanuts, pears, peppers, peppermint, pineapples, plantains, potatoes, pumpkins, soybeans, spearmint, squash, sweet potatoes, tobacco, tomatoes, watermelons, and yams. It is also used on non-bearing apple, cherry, citrus, peach, pear, and tobacco. Oxamyl is applied directly onto plants or the soil surface and is available in both liquid and granular form (though the granular form is banned in the U.S.). It has no residential use and is registered for use in EU countries.

Trade name

BLADE?; D-1410?; DPX 1410?; INSECTICIDE-NEMACIDE 1410?; OXAMYL CARBAMATE INSECTICIDE?; THIOXAMYL?; VYDATE?; VYDATE? 10G; VYDATE L?; VYDATE INSECTICIDE/NEMATICIDE?; VYDATE OXAMYL INSECTICIDE/NEMATOCIDE?[C]

Safety Profile

Poison by ingestion, skin contact, and inhalation. Experimental reproductive effects. Moderately toxic by skin contact. When heated to decomposition it emits very toxic fumes of NOx and SOx

Potential Exposure

Oxamyl is a white crystalline solid. Sulfur or garlic-like odor. Molecular weight=219.3

Environmental Fate

Soil. Oxamyl rapidly degraded in a loamy sand and fine sand soil at 25°C to carbon dioxide and the intermediate methyl N-hydroxy-N,N-dimethyl-1-thiooxaminidate (Rajagopol et al., 1984). The reported half-life in soil is approximately one week (Worthing and Hance, 1991). Ou and Rao (1986) reported a half-life in soil of 8–50 days. The reported half-lives of oxamyl in Pitstone, Devizes, Sutton Veany and Mepal soils at 15°C were reported to be 10.2–13.1, 6.2, 7.1 and 17.8 days, respectively (Bromilow et al., 1980). Smelt et al. (1987) reported that oxamyl degraded at a higher rate in field plots after repeated applications of this nematocide than in soils that received no treatment. The repeated applications of oxamyl to soils probably induced microbial activity, which resulted in the accelerated disappearance of this compound.Harvey and Han (1978) reported a half-life of 8 days for oxamyl in soil.Groundwater. According to the U.S. EPA (1986) oxamyl has a high potential to leach to groundwater.Plant. Dislodgable residues of oxamyl on cotton leaf 0, 24, 48, 72 and 96 hours after application (0.41 kg/ha) were 1.5, 1.1, 1.2, 0.85 and 0.76 mg/m2, respectively (Buck et al., 1980).Chemical/Physical. The hydrolysis half-lives of oxamyl in a sterile 1% ethanol/water solution at 25°C and pH values of 4.5, 6.0, 7.0 and 8.0, were 300, 17, 1.6 and 0.20 weeks, respectively (Chapman and Cole, 1982). Under alkaline conditions, oxam

Metabolic pathway

Oxamyl degrades in soils, plants and animals following common metabolic pathways. Primary degradation reactions include the hydrolysis of the carbamate ester to yield the corresponding oxyimidothioate and nitrile. Other major metabolic reactions include N-demethylation and the hydration/oxidation of the nitriles to the corresponding amides and acids. The majority of the oxamyl metabolites are recovered as conjugates in plants and animals. No metabolites containing the oxidised thiomethyl group were observed. The primary degradation/metabolic pathways of oxamyl are presented in Scheme 1.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN2991 Carbamate pesticides, liquid, toxic, flammable, flash point <23°C, Hazard Class: 6.1; Labels: 6.1-Poisonous material, 3-Flammable liquid.

Degradation

Oxamyl (1) was stable under acidic conditions but hydrolysed rapidly under basic conditions at 25 °C with DT50 values of >30 days at pH 5, 8 days at pH 7, and 3 hours at pH 9 (McNally and Wheeler, 1988). Cleavage of the methylcarbamoyl bond yielded methyl 2-( dimethylamino)- N-hydroxy-2-oxoethanimidothioate (2) as the primary hydrolysis product. Exposure to artificial sunlight enhanced the degradation of oxamyl in pH 5 solution (DT50 7 vs. >30 days) to yield compound 2 (McNally, 1988). Rapid degradation of oxamyl was also observed in natural water exposed to natural sunlight (DT50 <1 day, Harvey and Han, 1978a). Compound 2 and its geometrical isomer (3) were major products observed in natural and distilled water exposed to artificial and natural sunlight. Further hydrolysis yielded (dimethy1amino)oxoacetica cid (4) as a minor photodegradation product in natural water exposed to natural sunlight.

Incompatibilities

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 Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal 2264 Oxamyl practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Small quantities may be treated with alkali and buried in a landfill. 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.

Check Digit Verification of cas no

The CAS Registry Mumber 23135-22-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,1,3 and 5 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 23135-22:
(7*2)+(6*3)+(5*1)+(4*3)+(3*5)+(2*2)+(1*2)=70
70 % 10 = 0
So 23135-22-0 is a valid CAS Registry Number.

23135-22-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name oxamyl

1.2 Other means of identification

Product number -
Other names (EZ)-N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Insecticide
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:23135-22-0 SDS

23135-22-0Relevant articles and documents

A NOVEL CRYSTALLINE FORM OF OXAMYL, A PROCESS FOR ITS PREPARATION AND USE OF THE SAME

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Page/Page column 14-15, (2018/06/22)

The present invention describes a crystalline form of oxamyl of formula (I), a crystal preparation process, the analyses of the crystal through various analytical methods and using the crystalline form to prepare a stable agrochemical formulation. The invention also describes the use of various solvents towards the crystalline form preparation conditions.

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