Name | Isoproturon |
Synonyms | IPU ALON Alon Tolkan Arelon ALON(R) Graminon IPROFILE ISOGUARD Isoproturon Isoproturon W.P. 3-P-CUMENYL-1,1-DIMETHYLUREA 3-(4-ISOPROPYLPHENYL)-1,1-DIMETHYLUREA N-(4-Isopropylphenyl)-N',N'-dimethyl urea 1,1-dimethyl-3-[4-(propan-2-yl)phenyl]urea |
CAS | 34123-59-6 |
EINECS | 251-835-4 |
InChI | InChI=1/C12H18N2O/c1-9(2)10-5-7-11(8-6-10)13-12(15)14(3)4/h5-9H,1-4H3,(H,13,15) |
Molecular Formula | C12H18N2O |
Molar Mass | 206.28 |
Density | 1.0310 (rough estimate) |
Melting Point | 158° |
Boling Point | 345.15°C (rough estimate) |
Flash Point | 100°C |
Water Solubility | 60mg/L(20 ºC) |
Vapor Presure | 3.64E-05mmHg at 25°C |
Appearance | neat |
Color | White to Almost white |
Maximum wavelength(λmax) | ['240nm(H2O)(lit.)'] |
Merck | 14,5218 |
BRN | 2214033 |
pKa | 15.06±0.70(Predicted) |
Storage Condition | APPROX 4°C |
Refractive Index | 1.4760 (estimate) |
Physical and Chemical Properties | Pure colorless powder, melting point 155-156 ℃, vapor pressure 0.0033 MPa (20 ℃). Solubility (20 °c); 55g/L in water, 5g/L in benzene, 63g/L in methylene chloride. Acute oral LD50; Rats 1826-3600 mg/kg (body weight), mice 3350 mg/kg (body weight). A selective herbicide |
Use | Selective herbicides. Pre-and post-bud application to control annual grass weeds and broad-leaved weeds |
Risk Codes | R40 - Limited evidence of a carcinogenic effect R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36 - Irritating to the eyes R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
Safety Description | S36/37 - Wear suitable protective clothing and gloves. 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. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S16 - Keep away from sources of ignition. |
UN IDs | UN 3077 |
WGK Germany | 3 |
RTECS | YT0170000 |
HS Code | 29242990 |
Hazard Class | 9 |
Packing Group | III |
Toxicity | LD50 in mice, rats (mg/kg): 3350, 3600 orally (Thizy, 1972) |
Raw Materials | Dimethylamine o-Xylene |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
toxicity | acute oral LD50 of male rats is 1800mg/kg, female is 2400mg/kg; Toxicity test was carried out on rats for more than 30 days, and the non-acting dose was 500 mg/kg. |
use | is a selective herbicide isoproteron is a selective herbicide, which can be used before and after germination. It is used to control weeds such as wheat, barley, cotton, corn, soybeans, peas, broad beans, peanuts and other crops. The effect is poor. The recommended application amount is 12~22.5g active ingredient/100 m2. Mixed with grass spirit, the control of wild oats and broad-leaved weeds is better. Selective herbicide. Application before and after buds to control annual gramineous weeds and broadleaf weeds this product is a substituted urea herbicide that selectively interferes with weed photosynthesis. It is mainly used to control weeds such as wheat, soybean, cotton, corn and so on. |
Production method | It is obtained by the reaction of p-isopropylphenyl isocyanate and dimethylamine. Add the 33% dimethylamine aqueous solution to the reaction bottle, add water, cool to 0-5 ℃, accelerate stirring, and add p-isopropylphenyl isocyanate dropwise. Stir at 0-5 ℃ for 2h, filter, recrystallize the filter cake in acetone to obtain the finished product. Raw material consumption quota: p-isopropylaniline (95%)980kg/t, dimethylamine (40%)950kg/t, phosgene (80%)840kg/t, chlorine 570kg/t. isocyanate method isocyanate isopropyl ester preparation with toluene as solvent, 4-isopropylaniline and phosgene reaction to produce isopropyl isocyanate. The synthesis of isopropyl isocyanate isopropyl ester and dimethylamine are added to form isopropyl. The feeding process is isocyanate: dimethylamine = 1:1 (mol ratio); Dropping temperature 15 ℃, time 20min; Reaction temperature 20~30 ℃, time 2h. Using water as solvent, the yield is 95%. Carbamoyl chloride method first prepare N,N-dimethylcarbamoyl chloride; then react with 4-isopropylaniline to synthesize isopropylone. Preparation of Isohexyl Trichloroacetanilide by Non-phosgene Method 13.5g (0.1mol) p-isopropylaniline and 16.5g (0.1mol) trichloroacetic acid are mixed, 14.0g (0.1mol) phosphorus trichloride is added dropwise under stirring, the temperature is controlled at 100~110 ℃, the dripping is performed at a constant temperature for 30min, then 100mL of ice water is added, the solid is collected by suction filtration and washed with water to be neutral, and recrystallized with ethanol/water to obtain, M. p.123 ~ 125 ℃. Synthesis of Isopropylon 14.0g (0.05mol) of p-isopropyl trichloroacetanilide, 5.0g(0.125mol) of sodium hydroxide, 4.5g (0.10mol) of dimethylamine and 80mL of xylene sulfoxide were added to a reactor, reacted at 60~80 ℃ for 30min, the reaction was completed and poured into water, the solid was collected by suction filtration, and recrystallized with ethanol/water to obtain a white solid with a yield of 95%,m.p.152~154 ℃. According to Atanassova, I .A. reports, this reaction process may be that under the action of p-isopropyl trichloroacetanilide, the intermediate p-isopropyl isocyanate phenyl ester is first formed, and then immediately reacts with dimethylamine to form isopropyl alcohol. Isopropylone is synthesized by non-phosgene method, and urea can be used instead of phosgene. It reacts with p-isopropylaniline in aqueous solution to generate intermediate p-isopropylphenylene urea, and then reacts with dimethylamine aqueous solution to synthesize isopropylone. The total yield is 76%. |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |