Name | linuron |
Synonyms | LOROX Liron AFALON linuron LINUREX Norunil Provigil LOROX(R) Cephalon AFALON(R) AGRO-KIMOLIN Linuron Solution, 100ppm 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea 1-methoxy-1-methyl-3-(3,4-dichlorophenyl)urea n'-(3,4-dichlorophenyl)-n-methoxy-n-methyl-ure N-(3,4-Dichlorophenyl)-N'-methoxy-N'-methylurea |
CAS | 330-55-2 |
EINECS | 206-356-5 |
InChI | InChI=1/C9H10Cl2N2O2/c1-13(15-2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14) |
Molecular Formula | C9H10Cl2N2O2 |
Molar Mass | 249.09 |
Density | 1.4909 (rough estimate) |
Melting Point | 93-94°C |
Boling Point | 180-190°C |
Flash Point | 11°C |
Water Solubility | 0.0075 g/100 mL |
Solubility | Slightly soluble in water, soluble in acetone and ethanol |
Appearance | Solid |
Color | White |
BRN | 2128725 |
pKa | 12.13±0.70(Predicted) |
Storage Condition | APPROX 4°C |
Refractive Index | 1.6100 (estimate) |
MDL | MFCD00055249 |
Physical and Chemical Properties | Melting point 93-94°C boiling point 180-190°C water-soluble 0.0075g/100 mL |
Use | Urea herbicide, can be used for soybean, corn, cotton, carrot, celery, wheat, peanut, sugarcane, fruit and other crops |
Risk Codes | R61 - May cause harm to the unborn child R22 - Harmful if swallowed R40 - Limited evidence of a carcinogenic effect R48/22 - Harmful danger of serious damage to health by prolonged exposure if swallowed. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R62 - Possible risk of impaired fertility R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
Safety Description | S53 - Avoid exposure - obtain special instructions before use. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. S7 - Keep container tightly closed. |
UN IDs | UN 3077 |
WGK Germany | 3 |
RTECS | YS9100000 |
HS Code | 29280000 |
Toxicity | LD50 orally in rats: 1500 mg/kg (Bailey, White) |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
biological activity | Linuron is a phenylurea herbicide, widely used to control the growth of grasses and weeds in various crops and orchards. Linuron is a photosystem II inhibitor. Linuron is also a competitive androgen receptor (AR) antagonist with a Ki of 100 μM. It shows reproductive toxicity in animals and can be used as an endocrine disruptor. |
target | Ki: 100 μM (Androgen receptor) Photosystem II |
use | liguron can be used to control species, dicotyledonous weeds and some perennial weeds in corn, wheat, cotton, soybean, sorghum, peanut, pea, potato, upland rice, sunflower, sugarcane, flax, various vegetables, fruit trees, forest nurseries and other crop fields. The oral LD of rats was 4000mg/kg. It is a urea herbicide and can be used in soybeans, corn, cotton, carrots, celery, wheat, peanuts, sugarcane, fruit trees and other crops |
Production method | The 3, 4-dichlorobenzene isocyanate reacts with hydroxylamine sulfate to produce 3, 4-dichlorobenzene hydroxyurea, and then reacts with dimethyl sulfate to produce Liguron. Preparation of 1.3, 4-dichlorobenzene Hydroxyurea 3, 4-dichlorobenzene isocyanate-toluene solution, hydroxylamine sulfate aqueous solution and sodium hydroxide solution are respectively pumped into each metering tank according to the calculated amount. Water and hydroxylamine sulfate are added to the glass-lined reaction pot at the same time, stirred and cooled, sodium hydroxide solution is added dropwise at about 20 ℃ for about 1 hour, the temperature is controlled at about 20 ℃, and the pH value after dropwise addition is between 7.5 and 7.9 (otherwise, sodium hydroxide or hydroxylamine sulfate is added). Then start dropping 3,4-dichlorobenzene isocyanate-toluene solution. At this time, the temperature is controlled to 30±2 ℃, and the dropping is completed within about 1.5h, and the reaction is continued for 2h at this temperature. After standing for 2h, the upper toluene clear liquid was extracted. The lower material is mixed with water and then centrifuged to obtain solid wet product 3, 4-dichlorobenzene hydroxyurea. 87% yield. 2. Preparation of Liguron The above-mentioned wet hydroxyurea was added to the glaze-lined reaction kettle, then the calculated amount of dimethyl sulfate was added and stirred for 20min. 20% sodium hydroxide solution is added dropwise, the temperature is controlled at 20-30 ℃, and the dropwise solution is completed within about 1.5h. React at about 30 ℃ for 2h to pH7 as the end point of the reaction. If it is acidic, sodium hydroxide can be added appropriately. After the reaction, add water, stir, filter, and dry to obtain Liguron raw powder. 90% yield. |
category | pesticide |
toxicity classification | poisoning |
acute toxicity | oral-rat LD50: 1146 mg/kg; Oral-mouse LD50: 2400 mg/kg |
flammability hazard characteristics | Combustion produces toxic nitrogen oxides and chloride gases |
storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials storage and transportation |
fire extinguishing agent | dry powder, foam, sand |
occupational standard | STEL 1 mg/m3 |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |