Oryzalin

Oryzalin Property

Melting point:

141°C

Boiling point:

514.0±60.0 °C(Predicted)

Density 

1.2

refractive index 

1.6000 (estimate)

storage temp. 

0-6°C

solubility 

DMSO : 250 mg/mL (721.79 mM; Need ultrasonic)

pka

9.14±0.60(Predicted)

form 

Crystalline Solid

color 

Deep orange

Water Solubility 

85mg/L(25 ºC)

BRN 

2177305

Major Application

agriculture
environmental

InChI

1S/C12H18N4O6S/c1-3-5-14(6-4-2)12-10(15(17)18)7-9(23(13,21)22)8-11(12)16(19)20/h7-8H,3-6H2,1-2H3,(H2,13,21,22)

InChIKey

UNAHYJYOSSSJHH-UHFFFAOYSA-N

SMILES

CCCN(CCC)c1c(cc(cc1[N+]([O-])=O)S(N)(=O)=O)[N+]([O-])=O

LogP

3.730

CAS DataBase Reference

19044-88-3(CAS DataBase Reference)

NIST Chemistry Reference

Oryzalin(19044-88-3)

EPA Substance Registry System

Oryzalin (19044-88-3)

Safety

Hazard Codes 

N

Risk Statements 

51/53

Safety Statements 

60

RIDADR 

UN 3077

WGK Germany 

2

RTECS 

WO9350000

HS Code 

29350090

Storage Class

11 - Combustible Solids

Hazard Classifications

Aquatic Acute 1
Aquatic Chronic 1
Carc. 2
Skin Sens. 1
STOT RE 2

Hazardous Substances Data

19044-88-3(Hazardous Substances Data)

Toxicity

LD50 orally in rats: >10 g/kg (Decker, Johnson)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H351Suspected of causing cancer

H373May cause damage to organs through prolonged or repeated exposure

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P308+P313IF exposed or concerned: Get medical advice/attention.

Oryzalin Chemical Properties,Usage,Production

Chemical Properties

Yellow
orange crystalline solid or powder. Odorless.

Uses

Herbicide.

Definition

ChEBI: A sulfonamide that is benzenesulfonamide substituted at positions 3 and 5 by nitro groups and at position 4 by a dipropylamino group.

General Description

Yellow-orange crystals. Non corrosive. Used as an herbicide.

Reactivity Profile

A dinitroaniline derivative.

Agricultural Uses

Herbicide: Oryzalin is used to control annual grasses, herbaceous plants, woody shrubs, vines and broadleaf weeds on fruit and nut trees, soya beans, peas, sweet potatoes, berries, vine and crops, cotton, Christmas tree plantations, commercial/industrial and recreation area lawns, golf course turf, residential lawns and turf, ornamental and/or shade trees, nonagricultural rights-of-way, nonagricultural uncultivated and industrial areas, power stations, paths/patios and paved areas.

Trade name

AGVALUE®; COMPOUND 67019®; DIRIMAL®; EL-119®; EXCEL-S-PLUS®; EXPEDITE®; FLEXLAN®; NATIONS AG II®; ORYZA®; PRO-TECK®; ROUT®; RYCELAN®; RYZELAN®; SNAPSHOT®; SURFLAN®; TURF FERTILIZER®; XL 2G®

Safety Profile

Low toxicity by ingestion and skin contact. Mutation data reported. When heated to decomposition emits toxic fumes of NOx, SOx.

Synthesis

The synthesis method of oryzalin is as follows: Add PCl5 (624 mg, 3 mmol) to a suspension of 3,5-dinitro-N4,N4-di-n-propylsulfonate (347 mg) in dichloromethane (10 mL). Stir the reaction mixture for 2 hours. Wash the mixture with water. Collect the dichloromethane layer. Dry the dichloromethane layer with Na2SO4. Add 10 mL of 7N ammonia in methanol to the product. Stir the mixture for 3 hours at 40°C. Evaporate the solvent. Purify the product by silica gel column chromatography, eluting with hexane/ethyl acetate (2:1). Crystallize the product in dichloromethane/hexane.

Potential Exposure

Oryzalin is a 2,6-dinitroaniline herbicide used to control annual grasses, herbaceous plants, woody shrubs, vines, and broad leaf weeds on fruit and nut trees, soya beans, peas, sweet potatoes, berries, vine and crops, cotton, Christmas tree plantations, commercial/industrial and recreation area lawns, golf course turf, residential lawns and turf, ornamental, and/or shade trees, nonagricultural rights-of-way, nonagricultural uncultivated and industrial areas, power stations, paths/patios, and paved areas.

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneoushazardous material, Technical Name Required. UN1596 Dinotoanilines, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

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, and epoxides. Slowly hydrolyzes in water, releasing ammonia, and forming acetate salts. Decomposes at 265C releasing toxic oxides of nitrogen, sulfur, and carbon. Decomposed by strong ultraviolet light.

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] GAUTAM BHATTACHARYA. Synthesis and Antitubulin Activity of N1- and N4-Substituted 3,5-Dinitro Sulfanilamides against African Trypanosomes and Leishmania[J]. Journal of Medicinal Chemistry, 2004, 47 7: 1823-1832. DOI:10.1021/jm0304461.