Thidiazuron
Thidiazuron
CAS: 51707-55-2
Molecular Formula: C9H8N4OS
Thidiazuron - Names and Identifiers
| Name | Thidiazuron |
| Synonyms | TDZ Thidiazuron N-phenyl-N-1,2,3,-thiadiazol-5-yluree N-Phenyl-N'-1,2,3-thiodiazol-5-yl urea 1-phenyl-3-(1,2,3-thiadiazol-5-yl)urea N-Phenyl-N'-(1,2,3-thiadiazol-5-yl)urea 5-Phenylcarbamoylamino-1,2,3-Thiadiazole THIDIAZURON PESTANAL (1-PHENYL- 3-(1,2,3 5-(N-Phenylcarbonylamino)-1,2,3-thiadiazole 1-PHENYL-3-(1,2,3-THIADIAZOL-5-YL)UREA*P LANT CELL C Thidiazauron (1-Phenyl-3-(1,2,3-thiadiazol-5-yl)-harnstoff |
| CAS | 51707-55-2 |
| EINECS | 257-356-7 |
| InChI | InChI=1/C9H8N4OS/c14-9(12-8-6-10-13-15-8)11-7-4-2-1-3-5-7/h1-6H,(H2,11,12,14) |
| InChIKey | HFCYZXMHUIHAQI-UHFFFAOYSA-N |
Thidiazuron - Physico-chemical Properties
| Molecular Formula | C9H8N4OS |
| Molar Mass | 220.25 |
| Density | 1.3493 (rough estimate) |
| Melting Point | 213°C |
| Boling Point | 1·51 |
| Solubility | Soluble in dimethylformamide and dimethyl sulfoxide. |
| Appearance | neat |
| Merck | 13,9384 |
| BRN | 1078092 |
| pKa | 12.06±0.70(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.6390 (estimate) |
| MDL | MFCD00078723 |
| Physical and Chemical Properties | The pure product is a white odorless and tasteless crystalline solid. m.p.210 -212.5 °c (decomposition) (decomposition at 217 °c), vapor pressure 4 x 10-9Pa) (25 °c). Solubility at 25 ℃: dimethyl sulfoxide> 500g/L, dimethyl formamide> 500g/L, cyclohexanone 21.5g/L, acetone 8g/L, methanol 4.5g/L, ethyl acetate 0.8g/L, hexane 6mg/L, insoluble in aliphatic and aromatic hydrocarbons, solubility in water 31mg/L. Partition coefficient 59 (pH = 7.3). 200 deg C below the stability; Room temperature on the water stability, Half-Life> 24d; In the soil Half-Life <60d. |
| Use | Used as plant growth regulator, suitable for cotton and other leaf removal |
Thidiazuron - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S22 - Do not breathe dust. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 3 |
| RTECS | YU1395000 |
| Toxicity | LC50 (96-hour) for bluegill sun?sh, channel cat?sh and rainbow trout >1,000 mg/L (Hartley and Kidd, 1987); acute oral LD50 for rats >5,000 mg/kg (Hartley and Kidd, 1987), 5,350 mg/kg (RTECS, 1985). |
Thidiazuron - Reference
| Reference Show more | 1. Shao Pei, Zhang Zhao, Wang Lin, et al. Effects of expander treatment on polyphenol content and antioxidant activity of kiwifruit [J]. Modern food science and technology, 2018(5). 2. Zhao Luzhou, Xin Fang, Sun Tianzun, et al. Physiological Analysis of overwintering bud development of Panax ginseng -- Analysis of endogenous plant hormones based on HPLC-MS/MS [J]. Journal of Northeast Normal University: natural science edition 2020(1):127-135. |
Thidiazuron - Nature
Open Data Verified Data
pure white, odorless, tasteless crystalline solid. The melting point was 217 °c (decomposition). The solubility at 25 ℃ is (g/L): dimethyl sulfoxide> 500, dimethyl formamide> 500, cyclohexanone 21.5, acetone 8, methanol 4.5, ethyl acetate 0.8, hexane 6, insoluble in aliphatic and aromatic hydrocarbons, solubility in water 31mg/L.
Last Update：2024-01-02 23:10:35
Thidiazuron - Preparation Method
Open Data Verified Data
with diethyl carbonate as the starting material, thiazuron was prepared by hydrazine hydrolysis, addition, cyclization, amination and aminolysis.
Last Update：2022-01-01 10:13:19
Thidiazuron - Use
Open Data Verified Data
urea plant growth regulators, mainly used as cotton defoliant, can also be used for apple trees, grapes and beans, soybeans, peanuts and other crops. Can also be used for the prevention and control of Humulus scandens, dog grass, Ma Tang, watching moniae, creeping grass, pig and other weeds.
Last Update：2022-01-01 10:13:20
Thidiazuron - Safety
Open Data Verified Data
rat oral LD50>4000mg/kg. Mouse oral LD50>5000mg/kg. Rabbit percutaneous LD50>4000mg/kg. Rats inhaled LC50> 2.3 mg/L(4H). Rats fed 2 years without the effect of the dose of 200mg/kg, dogs fed 1 year without the effect of the dose of lo0 mg/kg. No carcinogenic, teratogenic, mutagenic. Quail oral LD50>3160mg/kg. Rainbow trout LC50>lOOOmg/L( 96H), Daphnia LC50> 10 mg/L(48h). Non-toxic to bees.
Last Update：2022-01-01 10:13:20
Thidiazuron - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| use | urea plant growth regulator with cytokinetin activity. Mainly used as cotton defoliant, but also used for apple trees, vines, hibiscus defoliation and kidney beans, soybeans, peanuts and other crops. It has obvious inhibitory effect, and the dosage is 0.3~3kg/hm2. If the dosage of cotton field is 0.5kg/hm2, when 50% ~ 60% cotton peach is opened, the medicine is used, the preparation is diluted into 500L/hm2 aqueous solution, sprayed on the plant, and the defoliation effect is 98%. It can also be used to control weeds such as barnyard grass, bermudagrass, Matang, Meiniang, creeping ice grass, pig disaster, etc., with a dosage of 3kg/hm2 and a control effect of nearly 100%. light yellow powder used for cotton defoliation, the dosage is 0.05~0.2kg/ha. Thepuron TDZ is a new and efficient cytokinin used in tissue culture, which can better promote plant bud differentiation. Used as a plant growth regulator, suitable for cotton defoliation |
| production method | preparation method-preparation of 1,2, 3-thiazadiazene -5-amine diazomethane method: dissolve 1.01g CH3CONCS in 10mL of dry ether, add about 0.5mol CH2N2 ether solution dropwise under stirring and cooling, and stir for 1h, about 0.39g 1,2, 3-thiadiazocene -5-acetamide was obtained. After mixing 2.21g of the above product with 4g of magnesium oxide, 120mL of acetone and 80mL of water, reflux reaction for 1h to obtain 0.85g of corresponding product (intermediate). Ammonolysis method: 20g of 5-chloro -1,2,3-thiadiazene was put into 60~70mL of liquid ammonia and stirred for 3.5h to obtain intermediate with 93.2% yield. The synthesis of thiazuron can be prepared by the general synthesis method of urea herbicides. 1,2, 3-thiazadiazene-5-amine reacts with phenyl isocyanate to produce thiazuron. Preparation method II using diethyl carbonate as the starting material, through hydrazinolysis, addition, cyclization, amination, ammonolysis 5 step reaction synthesis: equimolar diethyl carbonate and hydrazine hydrate in room temperature stirring for 1h, placed overnight, reduced pressure to evaporate excess water and ethanol, after treatment to obtain hydrazinyl ethyl acetate, the yield is 91.25%; then add hydrazinyl ethyl acetate plus deionized water dropwise to chloroacetaldehyde (diatomite plus deionized water treatment) solution, the temperature is 0~5 ℃, recrystallized with deionized water, the product yield is 74.45%, and 2-chloroethylhydrazinyl ethyl formate is prepared; add the previous product to dichlorosyl, react at room temperature for 2 hours, add 400mL of saturated sodium carbonate solution dropwise, then distilled steam, and the water layer is extracted with an extractant, the yield of the product is 46% to obtain 5-chloro-1, 2,3-thiadiazole; then add solvent, pass ammonia for 4 hours, evaporate the solvent under reduced pressure, add deionized water to dissolve the residue and extract, and the yield is 71.3% to obtain 5-Amino -1,2, 3-thiadiazole; the above product reacts with phenyl isocyanate in the presence of solvent and triethylamine to obtain thiazuron, and the product can be recrystallized in propanol, 31.21% yield. The process conditions of the synthesis route can be further optimized to improve the total yield. There are also the following synthetic routes reported in the literature: The third preparation method uses 1,2, 3-thiazadiazocene-5-formyl chloride to react with azide toluene, and the product reacts with aniline to obtain thiazuron. |
| category | pesticide |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 5350 mg/kg; Oral-mouse LD50: 3740 mg/kg |
| flammability hazard characteristics | Combustion produces toxic nitrogen oxides and sulfur oxide 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 |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:50
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