Name | Daimuron |
Synonyms | Dymron Shouron Dymrone Daimuron 1-(4-methylphenyl)-3-(2-phenylpropan-2-yl)urea |
CAS | 42609-52-9 |
InChI | InChI=1/C17H20N2O/c1-13-9-11-15(12-10-13)18-16(20)19-17(2,3)14-7-5-4-6-8-14/h4-12H,1-3H3,(H2,18,19,20) |
Molecular Formula | C17H20N2O |
Molar Mass | 268.35 |
Density | 1.108g/cm3 |
Boling Point | 394.4°C at 760 mmHg |
Flash Point | 134°C |
Vapor Presure | 1.99E-06mmHg at 25°C |
Storage Condition | 2-8℃ |
Refractive Index | 1.594 |
pure product is white needle crystal. m.p.203 C. Solubility at 20 ℃ is: methanol, ethanol 1%, acetone, ether 10%, dimethylformamide 18.2%, dimethylsulfoxide 20%, insoluble in water. The pH value is in the range of 2~10 and is stable under heating and ultraviolet light irradiation. It can be hydrolyzed by boiling in 1mol/L hydrochloric acid for 6 hours. In the soil, the half-life is 49d,120d disappears 90%
the acute oral LD50 of male rats is 4000mg/kg, and that of male mice is 6500mg/kg; the acute percutaneous LD50 of rats and mice is about 3500mg/kg. Chronic toxicity test found no teratogenic, carcinogenic, mutagenic effect. Carp LC50 is 300mg/L (48h).
A selective substituted urea herbicide of the systemic conduction type. However, it is different from general ureas in chemical structure and mode of action. It has the following characteristics: ①It has special effects on Cyperaceae weeds, and it is best to use chemicals for soil treatment from 1 month before germination to germination; ②Whether in light or dark, it has a strong inhibitory effect on the germination of sensitive plants. It is not a photosynthesis inhibitor; ③It is absorbed by plant roots, it can significantly inhibit the elongation of roots and underground stems, so as to control the growth of the above-ground part, so its effect is delayed; ④ Soil surface treatment or weed stem and leaf treatment is ineffective, and only when the soil is mixed treatment is highly effective. It is suitable for controlling many weeds in rice, cotton, wheat, corn, soybean, watermelon, tomato, lettuce, carrot, radish and other crop fields, such as beef felt grass, special sedge, firefly, three-sided grass, veal aconite, flat stalks, two-way fluttering grass, etc. The standard dosage is 7 ~ 10kg active ingredient/hm2. For example, to control paddy field pilosa and scallus scallus, use 5.0% wettable powder 45~150g/100 m2; Control paddy field cattle hair grass, medication 7.5~15g/100 m2. The amount of medicine used to control weeds in dryland is much higher than that in paddy fields, and it is used before buds
New substituted urea herbicides. Whether in light or dark, it has a strong inhibitory effect on the germination of sensitive plants, so this product is not an inhibitor of photosynthesis. The product is absorbed by the roots of plants and can significantly inhibit the elongation of the roots and underground stems, thereby controlling the growth of the above-ground parts, so its effect is delayed. It has special effects on Cyperaceae weeds, and can safely prevent and remove the special-shaped fallen grass, three-sided grass, and cattle hair grass of rice, cotton, corn, soybeans and other crops, and the effect is good
36 parts of p-toluidine are dissolved in 35 parts of 35% hydrochloric acid and 300 parts of water, 25.3 parts of 90% sodium cyanate are added under stirring, reacted at 30 ℃ for 1h, 21 parts of 10% hydrochloric acid are added within half an hour, reacted for 10min, filtered, washed with water and dried to obtain p-tolyl urea. 11.3 parts of p-tolylurea were suspended in 80 parts of acetonitrile, 7.7 parts of α,α-dimethylbenzyl chloride and 24 parts of α-methylstyrene, stirred continuously, reacted at 60 ℃ for 6h, let stand, precipitate crystallization, filter, wash, and recrystallize with methanol to obtain salperone. The newer production method is to make α,α-dimethylbenzyl chloride react with sodium cyanate in a non-aqueous organic solvent and in the presence of a metal chloride catalyst to produce α,α-dimethylbenzyl isocyanic acid, and then Add to p-toluidine and desapuron, the content is greater than 95%.
p-tolurea method
Preparation of p-toluamide Sodium cyanate reacts with p-toluidine hydrochloride aqueous solution, the reaction temperature is controlled at 30 ℃, and the sodium cyanate is slightly excessive to prepare p-toluamide. Sodium cyanate can be calcined with urea and sodium carbonate.
Chlorinated cumene to prepare 2-phenylpropylene is added with hydrogen chloride in acetonitrile solvent, and chlorine atoms are introduced into the side chain to generate chlorinated cumene.
The synthesis of scaburon by the reaction of p-tolurea and chloropene, the synthesis of scaburon. 0.15mol of p-tolurea, 0.1mol of cumene chloride, 48g of α-methylstyrene and 160g of acetonitrile were added, stirred and reacted at 40 ℃ for 6h, standing at room temperature, 32g of crystallization was separated, and the yield was 80%.
α,α-dimethylbenzyl isocyanate method
This method is to react α,α-dimethylbenzyl chloride with sodium cyanate in the presence of a non-aqueous organic solvent and metal chloride catalyst to obtain α,α-dimethylbenzyl isocyanate, filter to remove the by-product sodium chloride, and then add with p-toluidine to obtain a good yield of grass-killing. For example, 50mL of ethyl acetate was added to the reactor, 6.5g (90mmol) of sodium cyanate, 0.5mol of zinc chloride and 1mmol of pyridine were 90%, stirred and heated to 50 ℃, and then 7.73g (50mmol) of α,α-dimethyl benzyl chloride was added to the reactor for 1h at 50 ℃. Preparation of α,α-dimethylbenzyl isocyanate. The addition of α,α-dimethylbenzyl isocyanate and p-toluidine to toluene or chlorobenzene gave almost a quantitative yield of scaloxone.
This method has mild reaction conditions, high yield, easy availability of raw materials, and less waste, and is recommended by people.
acid chloride method
This route has not been reported for industrial applications.