Oryzalin CAS 19044-88-3

Introduction：Basic information about Oryzalin CAS 19044-88-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Oryzalin Basic information

• Product Name: Oryzalin
• Synonyms: 4-(Dipropylamino)-3,5-dinitrobenzenesulfonimidic acid;Benzenesulfonamide, 4-(dipropylamino)-3,5-dinitro-;Dirimal;dirimalextra;EL 119;el-119;N(Sup4),N(Sup4)-Dipropyl-3,5-dinitrosulfanilamide;N4,N4-Dipropyl-3,5-dinitrosulfanilamide
• CAS: 19044-88-3
• MF: C12H18N4O6S
• MW: 346.36
• EINECS: 242-777-0
• Product Categories: Alpha sort;Alphabetic;AmidePesticides&Metabolites;DinitroanilinePesticides&Metabolites;Herbicides;N-PAnalytical Standards;O;Pesticides&Metabolites;DinitroanilineAnalytical Standards
• Mol File: 19044-88-3.mol

Oryzalin Chemical Properties

• 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 Information

• 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)

Oryzalin Usage And Synthesis

Chemical Properties

Yelloworange 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, herbaceousplants, woody shrubs, vines and broadleaf weedson fruit and nut trees, soya beans, peas, sweet potatoes,berries, vine and crops, cotton, Christmas tree plantations,commercial/industrial and recreation area lawns, golfcourse turf, residential lawns and turf, ornamental and/orshade trees, nonagricultural rights-of-way, nonagriculturaluncultivated and industrial areas, power stations, paths/patiosand 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 herbicideused to control annual grasses, herbaceous plants,woody shrubs, vines, and broad leaf weeds on fruit and nuttrees, soya beans, peas, sweet potatoes, berries, vine andcrops, cotton, Christmas tree plantations, commercial/industrialand recreation area lawns, golf course turf, residentiallawns and turf, ornamental, and/or shade trees, nonagriculturalrights-of-way, nonagricultural uncultivated and industrialareas, power stations, paths/patios, and paved areas.

Shipping

UN3077 Environmentally hazardous substances,solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneoushazardousmaterial, 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 inwater, 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 drainsor sewers. Dispose of waste material as hazardous wasteusing a licensed disposal contractor to an approved landfill.Consult with environmental regulatory agencies for guidanceon acceptable disposal practices. Incineration witheffluent gas scrubbing is recommended. Containers must bedisposed of properly by following package label directionsor by contacting your local or federal environmental controlagency, 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.