Subdue
Metalaxyl
CAS: 57837-19-1
Molecular Formula: C15H21NO4
Subdue - Names and Identifiers
| Name | Metalaxyl |
| Synonyms | Subdue subdue2e Metalaxyl ridomil2e Acylon(Ciba-Geigy) methyl N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate n-(methoxyacetyl)-n-(2,6-xylyl)-,methylester,dl-alanin methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninate n-(2,6-dimethylphenyl)-n-(methoxyacetyl)-dl-alaninmethylester N-(2,6-Dimethylphenyl)-N-(methoxy acetyl)-alanine methyl ester n-(2,6-dimethylphenyl)-n-(methoxyacetyl)-dl-alaninemethylester |
| CAS | 57837-19-1 |
| EINECS | 260-979-7 |
| InChI | InChI=1/C15H21NO4/c1-10-7-6-8-11(2)14(10)16(13(17)9-19-4)12(3)15(18)20-5/h6-8,12H,9H2,1-5H3 |
Subdue - Physico-chemical Properties
| Molecular Formula | C15H21NO4 |
| Molar Mass | 279.33 |
| Density | 1.1083 (rough estimate) |
| Melting Point | 72-73°C |
| Boling Point | 422.1°C (rough estimate) |
| Flash Point | 100°C |
| Water Solubility | 0.84 g/100 mL |
| Solubility | Chloroform (Slightly), Methanol (Slightly) |
| Vapor Presure | 7.5 x 10-4 Pa (25 °C) |
| Appearance | neat |
| Color | Off-White to Pale Beige |
| BRN | 2947777 |
| pKa | 1.41±0.50(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.5130 (estimate) |
| Physical and Chemical Properties | Melting Point 72-73°C water-soluble 0.84g/100 mL |
| Use | It is an systemic fungicide, used as a fungicide for tobacco, rubber tree, grape, hops, fruits, vegetables and other |
Subdue - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R43 - May cause sensitization by skin contact 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 |
| Safety Description | S13 - Keep away from food, drink and animal foodstuffs. S24 - Avoid contact with skin. S37 - Wear suitable gloves. S46 - If swallowed, seek medical advice immediately and show this container or label. 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. S16 - Keep away from sources of ignition. |
| UN IDs | UN 1648 3/PG 2 |
| WGK Germany | 2 |
| RTECS | AY6910000 |
| HS Code | 29242990 |
| Toxicity | LD50 in rats (mg/kg): 669 orally (Urech) |
Subdue - Upstream Downstream Industry
Subdue - Nature
Open Data Verified Data
white crystals. The melting point is 71~72 ℃, the vapor pressure (20 ℃)2.933 × 10 -4 Pa, the relative density (20 ℃)1.21. Soluble in a variety of organic solvents, methanol solubility of 65%; Water solubility (20 degrees C) of 0.71%. It is more stable in acidic and neutral medium. Non-flammable, non-explosive, non-corrosive.
Last Update：2025-06-10 22:55:16
Subdue - Preparation Method
Open Data Verified Data
first, three compounds of methyl a-chloropropionate, 2, 6-dimethylaniline and methoxyacetic acid were prepared. Finally, metalaxyl was prepared. (1) chloropropionic acid and methanol are directly esterified under the condition of concentrated sulfuric acid as catalyst, anhydrous calcium chloride is added as dehydrating agent, and the reaction is stirred at 50~60 ° C. To obtain methyl a-chloropropionate. Methyl a-chloropropionate can also be prepared by reacting phosgene with a-chloropropionic acid to form a-chloropropionyl chloride and then reacting with methanol. (2) nitration of M-xylene with mixed acid, separation of 2,4-= methylnitrobenzene to give 2. 6-= methylnitrobenzene, and reduction with hydrogen to give 2,6-methylaniline. (3) ethylene glycol and methyl ether are oxidized with nitric acid, and the reaction is carried out under the action of a vanadium salt and a copper salt as a catalyst to obtain methoxyacetic acid. The 2,6-= methyl aniline obtained above was reacted with methyl a monochloropropionate, anhydrous sodium carbonate was used as acid binding agent, and a small amount of iodine catalyst was added to obtain N-(2 'methyl propionate). -2,6-= methylaniline. Methoxyacetic acid and appropriate amount of toluene were heated, phosphorus trichloride was added dropwise, and the reaction was continued. The lower phosphorous acid was removed to obtain methoxyacetyl chloride toluene solution, and then N-(2 '-methyl propionate)-2 was added dropwise. 6-= The Reflux reaction of methylaniline was continued, and metalaxyl was obtained by treatment.
Last Update：2022-01-01 10:12:23
Subdue - 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. 1. Sample Preparation This standard substance is made of metalaxyl pure product with accurate purity and fixed value as raw material, chromatographic methanol as solvent, and accurately configured by weight-volume method. Metalaxyl, English name: Metalaxyl,CAS No.: 57837-19-1 2. Traceability and Setting Method This standard substance takes the configuration value as the standard value, and uses high performance liquid chromatography-ultraviolet detector (HPLC-VWD) to compare this batch of standard substances with quality control control samples 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)BW10304 The uncertainty of metalaxyl 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: ice bags should be transported, and extrusion and collision should be avoided during transportation; storage under freezing 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 17:26:34
Subdue - Application
Open Data Verified Data
A new type of high efficiency disinfectant. Can be absorbed into the plant, the water solubility is much higher than the general fungicide. It has selective effects on the Frost mold and Phytophthora in the class Oomycetes, such as potato late blight, grape downy mildew, hop downy mildew, sugar beet blight, rape white Rust, tobacco black shank and so on have good control effect. Also can be used for cotton sudden fall disease, Millet White Disease, good control effect.
Last Update：2025-08-19 16:24:40
Subdue - Safety
Open Data Verified Data
The oral LD50 of male rats and mice was 66 9mg/kg, and the percutaneous LD50 of rats was> 3100mg/kg. Rats 2 years feeding test no effect of the dose of/50mg/kg (equivalent to 2.5mg/kg per day), under the experimental conditions, no animal has carcinogenic, teratogenic, mutagenic effects. The third generation reproductive test showed no abnormality. Carp, rainbow trout LC50 lOOmg/L; Bee LCso 20ug/only; Quail LC50 798~1067mg/kg.
Last Update：2022-01-01 10:12:24
Subdue - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | Metalaxyl is a phenylamide fungicide, which was first developed by the Swiss company (now Syngenta), in the 90's of last century, it was a new type of high efficient internal absorption bactericide exclusively produced by Jiangsu Baoling Chemical Co., Ltd. Can be absorbed into the plant, the water solubility is much higher than the general fungicide. It has selective effects on the Frost mold and Phytophthora in the class Oomycetes, such as potato late blight, grape downy mildew, hop downy mildew, sugar beet blight, rape white Rust, tobacco black shank and so on have good control effect. |
| advantages | Metalaxyl is a new type of high-efficiency systemic fungicide, with dual effects of protection and treatment, low toxicity, low residue, and long-term efficacy is the advantage of metalaxyl, often do medicament soaking, foliar spraying and soil sterilization. |
| toxicity | The acute oral LD50 in male rats and mice was mg/kg, acute percutaneous LD50>3100mg/kg in rats. The no-effect dose for the 2-year feeding test in rats was 50mg/kg (relative to 2.5mg/kg per day). Under the experimental conditions, no animal has carcinogenic, teratogenic and mutagenic effects. The third generation reproductive test showed no abnormality. Carp, rainbow trout LC50100mg/L; Bee LD50 is 20g/only; Quail LD50 is 798~1067mg/kg. |
| Use | high efficiency systemic fungicide with protective and therapeutic effects. It has special effects on diseases caused by oomycetes, such as downy mildew of cucurbits, vegetables, grapes, tobacco, potato late blight, tobacco black disease, etc. Such as grape downy mildew, with 100L water containing the original drug concentration of 30g spray, every 2 weeks 1 times, a total of 5 times, leaf control effect of 100%, can also be used for sudden onset of cotton, Millet white disease, control effect is also very ideal. jaliao'an is a new type of high-efficiency systemic fungicide. Can be absorbed into the plant, the water solubility is much higher than the general fungicide, can penetrate into the new lipid small oomycetes cell membrane, play a bactericidal role. Therefore, jialiaoan has selective effects on the Frost mold and Phytophthora in oomycetes, such as potato late blight, grape downy mildew, hop downy mildew, sugar beet blight, rape white Rust, tobacco black shank and so on have good control effect. The amount of the product is low, generally 200-300g (active ingredient)/hm2. It is an systemic fungicide, used as a fungicide for tobacco, rubber tree, grape, hops, fruits, vegetables and other |
| production method | 2, 6-dimethylaniline is reacted with methyl 2-bromopropionate in the presence of sodium bicarbonate, DL-N-(2, 6-dimethylphenyl)-α-aminopropionic acid methyl ester was obtained. Then, the acylation reaction was carried out with methoxy acetyl chloride, and thus, the aloxanone was obtained. preparation of methyl α-chloropropionate chloropropionic acid was directly esterified with methanol, concentrated sulfuric acid was used as catalyst, and anhydrous calcium chloride was used as dehydrating agent. The reaction was stirred at 50-60 °c for 8H. The upper layer of crude ester was added with water and adjusted to pH 6 with Na2CO3. After separation of the aqueous phase, methyl α-chloropropionate was obtained by distillation with a content of 97.7% and a yield of 91.8%. Methyl α-chloropropionate can also be prepared by reacting phosgene with α-chloropropionic acid to form α-chloropropionyl chloride and then reacting with methanol. Preparation of 2,6-dimethylaniline 2, 6-dimethylnitrobenzene was prepared by nitration of M-xylene with mixed acid (HNO3 + H2SO4) and separation of by-product 2, 4-dimethylnitrobenzene. It is then reduced with hydrogen to give 2,6-dimethylaniline. Preparation of methoxyacetic acid ethylene glycol-methyl ether was oxidized by nitric acid, the catalyst was vanadium salt and copper salt, stirred at 60~70 ℃ for 1H, stirred at 80~90 ℃ for 3H, then heated to 90~100 ℃, 37% formaldehyde solution was added, and the reaction was completed after reflux stirring for 1H. The fraction below 130 ° C. Was distilled off, and methoxyacetic acid was collected under reduced pressure, with a content of 96.7% and a yield of 86.8%. Methoxyacetic acid can also be prepared by reacting chloroacetic acid with sodium methoxide. Preparation of N-(2 '-propionic acid methyl ester)-2, 6-dimethylaniline 2, 6-dimethylaniline was reacted with methyl α-chloropropionate, anhydrous sodium carbonate was used as acid binding agent, and a small amount of iodine catalyst was added, reflux at 120~140 ℃, azeotropic dehydration 24h, the end of the reaction, after treatment, the product content of 93.8%. Synthesis of metalaxyl methoxyacetic acid and appropriate amount of toluene were heated to 50~70 ℃, phosphorus trichloride was added dropwise, reaction was continued for 1H, cooled to room temperature, and the lower phosphorous acid was removed to obtain methoxyacetyl chloride toluene solution. After heating to slight reflux, N-(methyl 2 '-propionate)-2, 6-dimethylaniline was added dropwise, and the reaction was continued to reflux for 2H. The solvent was recovered, and solid crystals were obtained after the bottom of the bath was cooled, with a content of 89.0%, the yield was 98.6%. |
| category | pesticide |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 566 mg/kg |
| flammability hazard characteristics | toxic NOx gases from combustion |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored and transported separately from food raw materials |
| extinguishing agent | dry powder, foam, sand |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:09
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Raw Materials for Subdue