Phenmedipham Chemical Properties

Melting point:

140-144°C

Boiling point:

441.54°C (rough estimate)

Density 

1.1782 (rough estimate)

refractive index 

1.6240 (estimate)

Flash point:

100 °C

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

13.03±0.70(Predicted)

form 

Solid

color 

White to off-white

Water Solubility 

<0.1 g/100 mL at 21 ºC

BRN 

2395027

LogP

3.590

CAS DataBase Reference

13684-63-4(CAS DataBase Reference)

NIST Chemistry Reference

Methyl 3-m-tolylcarbamoyloxyphenylcarbamate(13684-63-4)

EPA Substance Registry System

Phenmedipham (13684-63-4)

Safety Information

Hazard Codes 

N

Risk Statements 

50/53

Safety Statements 

60-61

RIDADR 

UN 3077

WGK Germany 

2

RTECS 

FD9050000

Hazardous Substances Data

13684-63-4(Hazardous Substances Data)

Toxicity

(96-hour) for bluegill sunfish 3.98 mg/L, rainbow trout 1.4–3.0 mg/L, Daphnia magna 3.2 mg/L (Worthing and Hance, 1991), harlequin fish 16.5 mg/L (Hartley and Kidd, 1987); acute oral LD50 of pure phenmedipham and the formulated product for rats 3,700 and 10,300 mg/kg, respectively (Ashton and Monaco, 1991).

MSDS

• Language:English Provider:3-((Methoxycarbonyl)amino)phenyl (3-methylphenyl)carbamate

Phenmedipham Usage And Synthesis

Chemical Properties

Colorless crystalline solid, or needles; white powder. Odorless. Commercial product is available as an emulsifiable concentrate

Uses

Postemergence herbicide used to control weeds such as chickweed, dogfennel, foxtail, kochia, nightshade and yellow mustard, in strawberries, beet crops and spinach

Uses

Phenmedipham is an carbanilate selective herbicide used post-emergence in beet crops after the emergence of most broad-leaved weeds and before they develop.

Uses

Herbicide.

Definition

ChEBI: A carbamate ester that is (3-methylphenyl)carbamic acid in which the hydrogen of the hydroxy group has been replaced by a 3-[(methoxycarbonyl)amino]phenyl group.

General Description

Colorless crystals or white powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

3-((Methoxycarbonyl)amino)phenyl (3-methylphenyl)carbamate 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. 3-((Methoxycarbonyl)amino)phenyl (3-methylphenyl)carbamate is incompatible with alkaline preparations.

Fire Hazard

Flash point data for 3-((Methoxycarbonyl)amino)phenyl (3-methylphenyl)carbamate are not available, however 3-((Methoxycarbonyl)amino)phenyl (3-methylphenyl)carbamate is probably combustible.

Agricultural Uses

Herbicide: A post-emergence herbicide for control of annual broadleaf weeds and grasses in sugar beets, spinach, strawberries, and sunflowers

Trade name

AIMSAN®; BETAMIX® (phenmedipham + desmedipham); BETANAL®; CQ 1451® (phenmedipham + desmedipham + ethofumesate); EC herbicide (phenmedipham + desmedipham + ethofumesate); EP 452®; KEEPER®; KEMIFAM®; MSS HERBASAN®; NA 305® (phenmedipham + desmedipham + ethofumesate); NA 308® (phenmedipham + desmedipham + ethofumesate); POWERTWIN® (phenmedipham + ethofumesate); PROGRESS® (phenmedipham + desmedipham + ethofumesate); S-4075®; SCHERING 4072®; SN 38584®; SPINAID ®; SYNBETAN-P®; TWIN®; VANGARD®

Synthesis

Example 6: Preparation of methyl (3-(3-tolyl-carbamoyloxy)phenyl)carbamate Methyl N-(3-hydroxyphenyl)carbamate (8.35 g, 0.05 mol, prepared according to the method described in Example 1) was placed in a 150 mL beaker fitted with a stirrer, and water (75 mL) was added and stirred to mix. Borax (2.0 g) was added to the reaction system, followed by the slow dropwise addition of 3-tolyl isocyanate (5.3 g, 0.04 mol) through a dispensing funnel over a period of 45 minutes, with no need to adjust the temperature during the reaction. The pH was maintained at 9.2 during the reaction. after the dropwise addition, the reaction mixture was continued to be stirred for 1 hr. Upon completion of the reaction, the resulting finely suspended powdered product was filtered, washed with water and dried to afford the title compound (12.0 g, 100% yield, calculated on the basis of 3-tolyl isocyanate), melting point not determined.HPLC analysis showed the product to be 95.2% pure, with the remaining 4.8% consisting of unreacted N-(3-hydroxyphenyl)carbamic acid methyl ester and the by-products N,N'-di-3-tolylurea. -tolylurea.

Potential Exposure

A postemergence bis-carbamate/ carbamate ester herbicide used to control of annual broadleaf weeds and grasses in sugar beets, spinach, strawberries, and sunflowers.

Environmental Fate

Soil. Phenmedipham degraded in soil forming methyl N-(3-hydroxyphenyl)-carbamate and m-aminophenol (Hartley and Kidd, 1987). Hydrolysis yields m-aminophenol (Rajagopal et al., 1989). The reported half-life in soil is approximately 20 days (Rajagopal et al., 1989) and 26 days (Worthing and Hance, 1991)
Plant. In plants, methyl N-(3-hydroxyphenyl)carbamate is the major metabolite (Hartley and Kidd, 1987)
Photolytic. Bussacchini et al. (1985) studied the photolysis (λ = 254 nm) of phenmedipham in ethanol, ethanol/water and hexane as solvents. In their proposed free radical mechanism, homolysis of the carbon-oxygen bond of the carbamate linkage ga

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,

Incompatibilities

Decomposes .145C. Esters ith acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Carbamates are incompatible with reducing agents, strong acids, oxidizing acids, peroxides, and bases. Contact with active metals or nitrides cause the release of flammable, and potentially explosive, hydrogen gas. Releases oxides of nitrogen and carbon when heated to decomposition.

Waste Disposal

Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration with effluent gas scrubbing is recommended. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

References

[1] Patent: US4748265, 1988, A
[2] Patent: US4748265, 1988, A
[3] Patent: US4748265, 1988, A
[4] Patent: US4748265, 1988, A

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