Triadimenol(mixture of isomers)
Triadimenol
CAS: 55219-65-3
Molecular Formula: C14H18ClN3O2
Triadimenol(mixture of isomers) - Names and Identifiers
Triadimenol(mixture of isomers) - Physico-chemical Properties
| Molecular Formula | C14H18ClN3O2 |
| Molar Mass | 295.76 |
| Density | 1.2990 (rough estimate) |
| Melting Point | 112-117° |
| Boling Point | 465.4±55.0 °C(Predicted) |
| Flash Point | 2°C |
| Water Solubility | A 62 mg l-1 (20 °C); B 33 mg l-1(20 °C) |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Vapor Presure | A 6 x l0-7 Pa (20 °C); B 4 x l0-7 Pa (20 °C) |
| Appearance | neat |
| Color | White to Off-White |
| Merck | 13,9667 |
| BRN | 616470 |
| pKa | 13.29±0.20(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.5270 (estimate) |
| Physical and Chemical Properties | Melting Point: 110 ℃ |
| Use | It is a kind of systemic broad-spectrum triazole fungicide, which can kill the external and internal pathogens attached to seeds. |
Triadimenol(mixture of isomers) - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R52/53 - Harmful 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 R23 - Toxic by inhalation R20/22 - Harmful by inhalation and if swallowed. |
| Safety Description | S22 - Do not breathe dust. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | 2588 |
| WGK Germany | 2 |
| RTECS | KK2200000 |
| HS Code | 29339900 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 in male, female rats (mg/kg): 1161, 1105 orally; >5000 dermally, 24-hr; LD50 in quail: >10000 mg/kg (Frohberger) |
Triadimenol(mixture of isomers) - Upstream Downstream Industry
| Raw Materials | P-Chlorophenol hydrazine hydrate |
Triadimenol(mixture of isomers) - Introduction
This standard substance is mainly used for measuring instrument calibration, analytical method evaluation and quality control, as well as the content determination and residue detection of corresponding components in related fields such as food, hygiene, environment and agriculture. It can also be used for value traceability or as a standard liquid reserve solution. It is diluted step by step and configured into various standard solutions for work. Preparation of 1. Samples This standard substance is made of pure triadimenol with accurate purity and fixed value as raw material, chromatographic methanol as solvent, and accurately configured by weight-volume method. Triadimenol, English name: Triadimenol,CAS number: 55219-65-3 2. traceability and setting method This standard substance takes the configuration value as the standard value, and uses high performance liquid chromatography-diode array detector (HPLC-DAD) This batch of standard substances and quality control control samples are compared to verify the preparation value. By using preparation methods, measurement methods and measuring instruments that meet the requirements of metrological characteristics, the traceability of the value of the standard substance is guaranteed. 3. characteristic value and uncertainty (see certificate) number name standard value (ug/mL) relative expansion uncertainty (%)(k = 2)BW10246 The uncertainty of triadimenol 1002 standard value in methanol is mainly composed of raw material purity, weighing, constant volume, uniformity, stability and other uncertainty components. 4. uniformity test and stability inspection According to the JJF1343-2012 [General Principles and Statistical Principles of Standard Substance Setting], random sampling of sub-packed samples is carried out, uniformity test of solution concentration is carried out, and stability inspection is carried out. The results show that the standard material has good uniformity and stability. The standard substance is valid for 18 months from the date of setting the value. The development unit will continue to monitor the stability of the standard substance. If the value changes are found during the validity period, the user will be notified in time. 5. packaging, transportation and storage, use and precautions 1. Packaging: This standard substance is packed in borosilicate glass ampoules, about 1.2 mL/branch. When removing or diluting, the pipette quantity shall prevail. 2. Transportation and storage: normal temperature transportation, transportation should avoid extrusion and collision; Storage under refrigerated and dark conditions. 3. Use: Balance at room temperature (20±3 ℃) before unsealing, and shake well. Once the ampoule is opened, it should be used immediately and cannot be used as a standard substance after being fused again.
Last Update：2022-10-16 17:26:16
Triadimenol(mixture of isomers) - Reference Information
| 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 1161mg/kg, that of female is 1105mg/kg, and that of mice (female and male) is 1300mg/kg. Acute percutaneous LD50>5000mg/kg in rats. The non-effect dose of dog and rat feeding test for 90d was 600mg/kg per day. The LC50 of goldfish and rainbow trout were 10~15mg/L and 23.5mg/L respectively (both 96h). Quail LD50>1000mg/kg. No effect on bees. |
| use | broad-spectrum seed dressing fungicide, with systemic nature, can kill pathogenic bacteria attached to the surface and inside of seeds. Its bactericidal effect is to affect the biosynthesis of fungal ergosterol. Used to control powdery mildew and smut in cereal crops. Such as the control of wheat smut, net smut, root rot, barley smut, rust, leaf stripe, net spot, etc., every 100kg of seeds with 25% dry seed powder 30~50g, the control effect is more than 90%. For corn and sorghum head smut, 42~75g of 25% dry mix powder was used for seed dressing per 100kg of seeds, with a control effect of more than 90%. If 100kg of seeds were mixed with 30g triadimefol and 5g of wheat ear ning, the control effect on loose smut, scruple stripe, reticulum spot, root rot of spring barley and loose smut, net smut, snow rot of winter wheat, leaf stripe and loose smut of spring swallow wheat was 92% to 100%. triadimenol is a broad-spectrum fungicide with high efficiency and low toxicity. It is used to control wheat, rice rust, powdery mildew, sheath blight and other diseases, and has obvious yield increase effect. It can also be used as cereal seed treatment agent and control cereal head smut. is a systemic broad-spectrum triazole fungicide, which can kill germs attached to the outside and inside of seeds |
| production method | the synthesis of triadimenol is made from triadimefon by different reduction methods. The specific reduction method is as follows. 6.2g(0.03mol) aluminum isopropoxide dissolved in 62.5mL anhydrous isopropanol by aluminum isopropoxide method, adding 14.7g (0.05mol) triadimefon when stirred and heated to 50 ℃, continuing stirring and heating to 84 ℃, refluxing for 2-3h, distilled out 10-12mL of acetone and isopropanol mixed solvent, raised from 55 ℃ to 82 ℃, stopped heating, and distilled out the remaining solvent under reduced pressure. Add the residual liquid to 20mL of 10% sulfuric acid and 20mL of water under stirring, stir for 1.5h, precipitate white solid, filter, repeatedly wash the solid with 125mL of water, and dry to obtain triadimenol. The yield of triadimenol in this method is 81%, and the effective body is higher than that of other methods. The 65.8% of diastereomeric body a, body B 10.6%,m.p.129~132 ℃, purity 76.4% (literature value a body 85%, body B 11.5%,m.p.128~130 ℃). However, the reaction conditions are harsh and it is a good method for small batch production. Potassium borohydride method Triadimefon 32.9g (0.1mol) is dissolved in 150mL methanol, 5.4g (0.1mol) of potassium borohydride is added at 0~10 ℃, reacted at 5~10 ℃ for 2h, stirred at room temperature for 12h, cooled to 10 ℃, and 15g (0.16mol) concentrated hydrochloric acid is added. After adding, stir at room temperature for 6 hours, add 20g(0.24mol) of sodium bicarbonate dissolved in 190mL of water under intense stirring, and filter to obtain triadimenol. The method is convenient to operate and has high yield, but the boride resources are limited and the amount of boride in the reaction is large, which needs to be improved. The reported income rate reached 85%. M. p.112 ~ 117 ℃, the ratio of diastereomers was not determined. The yield of domestic research results reached 100%. The diastereomer A body is 34.7% and B body is 53%. M. p.112 ~ 114 ℃, purity 87.7%. The sodium hydrosulfite reduction method uses a cheap and easily available reducing agent sodium dithionite (sodium hydrosulfite) to reduce triadimefon to triadimenol in the presence of sodium bicarbonate in water and organic solvent systems. The process conditions are: triadimefon: sodium bicarbonate is 1:2:3 (mol), and the solvent system methanol: water is 1:(1~7). Preparation example: 0.01mol triadimefon (content 92.4%) and 10mL of methanol are mixed and completely dissolved, 70mL of aqueous solution containing 0.03mol of sodium bicarbonate is added, heated and refluxed, then 0.02mol of sodium hydrosulfite (content 98%) is added in batches within 4h, and refluxed for 2h after addition. Cool to room temperature, add 30mL of water and stir for 30min. Filter out the solid, wash with water, and dry to get a white solid. M. p.112 ~ 116 ℃. The content is 98.81% (mixed diastereomers) and the yield is 98.62%. If the same method is used, the solvent system is changed to dimethylformamide/water (volume ratio 1:1) to obtain a product yield of 99. 1%, the content is 98.84% (mixed diastereomer). The advantages of this method are low cost, simple process, and high yield and purity. See the reference [3] of this product for details. The hydrogen reduction method uses hydrogen to reduce, which needs to be carried out in the presence of a catalyst and a polar solvent. |
| category | pesticide |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 3800 mg/kg; Oral-mouse LD50: 3250 mg/kg |
| flammability hazard characteristics | combustible; combustion produces toxic nitrogen oxides and chloride 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 15:16:51
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Raw Materials for Triadimenol(mixture of isomers)