129909-90-6
Amicarbazone
CAS: 129909-90-6
Molecular Formula: C10H19N5O2
129909-90-6 - Names and Identifiers
| Name | Amicarbazone |
| Synonyms | Dinamic MKH3586 Micarbazone Amicarbazone Micarbazone(Dinamic AMICARBAZONE SOLUTION Amine azole metribuzin AMine azole Metribuzin 4-amino-5-oxo-3-propan-2-yl-n-tert-butyl-1,2,4-triazole-1-carboxamide 4-amino-N-tert-butyl-5-oxo-3-(propan-2-yl)-4,5-dihydro-1H-1,2,4-triazole-1-carboxamide 4-Amino-N-(1,1-dimethylethyl)-4,5-dihydro-3-(1-methylethyl)-5-oxo-1H-1,2,4-triazole-1-carboxamide |
| CAS | 129909-90-6 |
| InChI | InChI=1/C10H19N5O2/c1-6(2)7-13-15(9(17)14(7)11)8(16)12-10(3,4)5/h6H,11H2,1-5H3,(H,12,16) |
129909-90-6 - Physico-chemical Properties
| Molecular Formula | C10H19N5O2 |
| Molar Mass | 241.29 |
| Density | 1.12 |
| Melting Point | 137.5° |
| Boling Point | 350℃ at 101.3kPa |
| Solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) |
| Vapor Presure | 0-0Pa at 20-25℃ |
| Appearance | Solid |
| Color | White to Off-White |
| pKa | 17.04±0.20(Predicted) |
| Storage Condition | 2-8°C(protect from light) |
| Stability | Air Sensitive |
| Refractive Index | 1.586 |
129909-90-6 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 20/22 - Harmful by inhalation and if swallowed. |
| Toxicity | LD50 in rats (mg/kg): 1015 orally; >2000 dermally; LC50 in rats (4 hr): 2.242 mg/l air; LC50 in bluegill sunfish, rainbow trout (96 hr): >129, >120 mg/l (Philbrook) |
129909-90-6 - Reference Information
| LogP | 1.18 at 25℃ |
| surface tension | 62mN/m at 1g/L and 20 ℃ |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| triazolinone herbicide | amidazolinone is a triazolinone herbicide, which was successfully developed by the plant protection department of Bayer pharmaceutical company in Germany in 1988. amidazolinone is an inhibitor of photosynthesis. the typical symptoms of sensitive plants are chlorination, stop growth, yellow tissue and final death, it has cross resistance with other photosynthesis inhibitors (such as triazine herbicides), mainly through root and leaf absorption. The main annual broadleaf weeds on maize and sugarcane and many annual gramineous weeds on sugarcane can be effectively controlled. On corn, it has excellent control effect on Abutilon, Chenopodium, Wild Amaranth, Penn Xanthium and Sweet Potato, with an application amount of 500g ai/hm2; It can also effectively prevent and control Ze lacquer, sweet potato, forearm grass and Tribulus terrestris on sugarcane, with an application amount of 500g ~ 1200g ai/hm2. Its contact killing and holding effect determine that it has a wide application period, and it can be conveniently selected for soil use before planting or before budding. When used for sugarcane, it can also be applied after budding. It is used for less cultivated land, and its dosage is about 1/3~1/2 of atrazine. Amidoxafone is expected to partially or completely replace high-dose herbicides that control dicotyledonous broadleaf weeds and herbicides that are restricted to protect arable land. Aminazolidone can be mixed with many commercial herbicides to further expand the control spectrum and improve the efficacy. fig. 1 is the chemical structural formula of amazolone. |
| toxicity | female rats acute oral LD50>1015mg/kg, rats acute percutaneous LD50>2000mg/kg, no teratogenic, carcinogenic, mutagenic and regenerative toxicity. Acute oral LD50 of quail> 2000 mg/kg, LC50 of blue gill fish (96h)>129mg/L, and oral LD50 of bee> 24.8 μg/bee. |
| synthesis method | 1, synthesis of tert-butyl isocyanate add 73g of tert-butylamine and 100mL of o-dichlorobenzene to 1000 mL of a three-mouth flask with stirrer, thermometer and dropping funnel. after dissolution, add a solution composed of 96 g NaOH and 400 mL of water, 120g phosgene solution dissolved in 300mL of o-dichlorobenzene was added dropwise at 0~5 ℃ for 1 h, then reacted under severe stirring for 1 h, let it stand for stratification, and rectified to obtain 73g of tert-butyl isocyanate with 73% yield. 2. synthesis of diazolone add 44.1g(0.5 mol) isobutyric acid and 100mL toluene to a 500mL three-mouth flask with a stirrer, thermometer and dropping funnel, add 30g(0.6mol) hydrazine hydrate dropwise at room temperature under stirring, add catalyst isopropoxytitanium, heat reflux with water, filter to remove catalyst, add 200mL toluene into filtrate, within 2h, 60g of phosgene was introduced and desoluted under reduced pressure to obtain 62.4g of diazolone with 97.5% yield. 3, 4-amino -3-isopropyl -5-oxygen -1-H-1,2,4-triazole (triazolinone) synthesis in a three-mouth flask with a stirrer, thermometer and dropping funnel, add 53g(1.05mol) hydrazine hydrate, add 15.6g(0.195mol)50% NaOH solution dropwise under stirring, and heat to reflux within 1h after dropping, 132g(1.0mol diazolone) was added dropwise, reacted at 100 ℃ for 5h, cooled, toluene and water were added, pH was adjusted to 7 with sulfuric acid, filtered, the filter cake was washed with toluene and water respectively and vacuum dried at 60 ℃ to obtain 138g triazolinone with 93% yield. 4. synthesis 72.8g of triazolinone (0.5 mol), 0.8gKOH, 0.5gLiCl and 500mL of methyl acetate were added to the reaction bottle, heated to 60 ℃, 54g of tert-butyl isocyanate (0.55 mol) was added dropwise, refluxed for 3h, cooled, filtered to remove the catalyst, the filtrate was dedissolved, and the residue was vacuum dried at 60 ℃. 122g of amidoxone was obtained with 93.2% content and 94% yield. |
| Biological activity | Amicarbazone(BAY-MKH3586; BAY314666) becomes an effective inhibitor of photosynthetic electron transport by combining with the Qb domain of photosystem II(PSII); herbicide with broad-spectrum weed control. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:49:11
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