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Home > Encyclopedia > Isoproturon

Isoproturon

Isoproturon structure

Isoproturon 

structure
  • CAS No:

    34123-59-6

  • Formula:

    C12H18N2O

  • Chemical Name:

    Isoproturon

  • Synonyms:

    Urea,N,N-dimethyl-N′-[4-(1-methylethyl)phenyl]-;Urea,3-p-cumenyl-1,1-dimethyl-;N,N-Dimethyl-N′-[4-(1-methylethyl)phenyl]urea;N′-(p-Cumenyl)-N,N-dimethylurea;N-(4-Isopropylphenyl)-N′,N′-dimethylurea;DPX 6774;N′-(4-Isopropylphenyl)-N,N-dimethylurea;Isoproturon;Ipuron;HOE 16410;Arelon;Arelon R;Graminon;CGA 18731;CL 12150;Tolkan;Hytane 500L;3-(4-Isopropylphenyl)-1,1-dimethylurea;IP 50;N′-(p-Isopropylphenyl)-N,N-dimethylurea;Nocilon;IP-Flo;IPU Stefes;Alon;Alon (pesticide);Protugan;N,N-Dimethyl-N′-(4-isopropylphenyl)urea;Tolkan Flo;Hora-Flo;Isoflo (herbicide);Isoflo;Arelon Dyspersyjny;Izoturon;Iralon;Harpun;Isogard;Stefes IPU;Arelon Top 500SC;1-(4-Isopropylphenyl)-3,3-dimethylurea

  • Categories:

    Agrochemicals  >  Herbicides

Description

White Solid

Isoproturon Basic Attributes

206.28

206.28

251-835-4

2924299039

Characteristics

32.3

2.32

colorless solid

1.1±0.1 g/cm3

158 °C

353.2±25.0 °C at 760 mmHg

100 °C

1.555

60mg/L(20 ºC)

APPROX 4°C

LD50 in mice, rats (mg/kg): 3350, 3600 orally (Thizy, 1972)

Safety Information

III

9

UN 3077

3

40-50/53-36-20/21/22-11

36/37-60-61-26-16

YT0170000

Xi;N,N,Xi,Xn,F

Stable at normal temperatures and pressures.

P273-P281-P501

H332-H351-H410

Isoproturon Use and Manufacturing

Methods of Manufacturing

Isocyanate Preparation of Cumene Isocyanate Using toluene as a solvent, 4-isopropylaniline reacts with phosgene to generate cumene isocyanate. The synthesis of isopropanol cumene isocyanate and dimethylamine are added to form isopropanol. The feeding material is isocyanate: dimethylamine = 1:1 (mol ratio); dropwise addition temperature 15℃, time 20min; reaction temperature 20~30℃, time 2h. With water as the solvent, the yield is 95%. The carbamoyl chloride method first prepares the preparation of N, N-dimethylcarbamoyl chloride; then it reacts with 4-isopropylaniline to synthesize isopropylone. Non-phosgene method for the preparation of isopropyltrichloroacetanilide 13.5g (0.1mol) p-isopropylaniline and 16.5g (0.1mol) trichloroacetic acid were mixed, and 14.0g (0.1mol) trichloroacetic acid was added dropwise with stirring Phosphorus chloride, the temperature is controlled at 100~110℃, the reaction is continued for 30 minutes after dropping, then 100 mL of ice water is added, the solid is collected by suction filtration and washed with water until neutral, and recrystallized with ethanol/water to obtain white crystals with a yield of 91%. mp123~125℃. Synthesis of isopropylone 14.0g (0.05mol) p-isopropyltrichloroacetanilide, 5.0g (0.125mol) sodium hydroxide, 4.5g (0.10mol) dimethylamine and 80mL xylene sulfoxide were added to the reactor After reaction at 60~80℃ for 30min, the reaction was poured into water, the solid was collected by suction filtration, and recrystallized with ethanol/water to obtain a white solid, yield 95%, mp152~154℃. According to Atanassova, IA, the reaction process may be that the isopropyl trichloroacetanilide under the action of a base first generates intermediate phenyl isopropyl isocyanate, and then immediately reacts with dimethylamine to generate isopropyl alcohol . Isopropyl is synthesized by non-phosgene method, and urea can also be used to replace phosgene. It reacts with p-isopropylaniline in aqueous solution to form intermediate p-cumyl urea, and then reacts with dimethylamine aqueous solution to synthesize isopropyl Long, the total yield reached 76%.

Uses

Pre-and post-emergence herbicide for control of annual grasses and broad-leaved weeds. Herbicide.

Computed Properties

Molecular Weight:206.28
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:206.141913202
Monoisotopic Mass:206.141913202
Topological Polar Surface Area:32.3
Heavy Atom Count:15
Complexity:206
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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