2-(2-BENZOTHIAZOLYLOXY)-N-METHYLACETANILIDE
Mefenacet
CAS: 73250-68-7
Molecular Formula: C16H14N2O2S
2-(2-BENZOTHIAZOLYLOXY)-N-METHYLACETANILIDE - Names and Identifiers
| Name | Mefenacet |
| Synonyms | Mefenacet Hinochloa Mephenacet Bay FOE 1976 2-benzothiazol-2-yloxy-N-mehtylacetanilide 2-(2-BENZOTHIAZOLYLOXY)-N-METHYLACETANILIDE N-Methyl-N-phenyl(2-benzothiazolyloxy)acetamide 2-(1,3-benzothiazol-2-yloxy)-n-methylacetanilide 2-(2-Benzothiazolyloxy)-N-methyl-N-phenylacetamide N-Phenyl-N-methyl-2-(benzothiazol-2-yloxy)acetamide 2-(1,3-benzothiazol-2-yloxy)-N-methyl-N-phenylacetamide 2-(benzothiazol-2-yloxy)-N-methyl-N-phenylacetamide mefenacet |
| CAS | 73250-68-7 |
| EINECS | 277-328-8 |
| InChI | InChI=1/C16H14N2O2S/c1-18(12-7-3-2-4-8-12)15(19)11-20-16-17-13-9-5-6-10-14(13)21-16/h2-10H,11H2,1H3 |
2-(2-BENZOTHIAZOLYLOXY)-N-METHYLACETANILIDE - Physico-chemical Properties
| Molecular Formula | C16H14N2O2S |
| Molar Mass | 298.36 |
| Density | 1.2361 (rough estimate) |
| Melting Point | 134.8° |
| Boling Point | 441.0±47.0 °C(Predicted) |
| Flash Point | >100°C |
| Vapor Presure | 5.63E-08mmHg at 25°C |
| Appearance | neat |
| BRN | 1143987 |
| pKa | 1.53±0.10(Predicted) |
| Storage Condition | 0-6°C |
| Refractive Index | 1.6000 (estimate) |
| Physical and Chemical Properties | Pure white crystals. m.p.134.8 °c, vapor pressure 11 x 10-3Pa (100 °c). The solubility in organic solvent is: dichloromethane> 200g/L, dimethyl sulfoxide 110 ~ 220g/L, acetone 60 ~ 100g/L, acetonitrile 30 ~ 60g/L, ethyl acetate 20~50g/L, toluene 20~50g/L, isopropanol 5~10g/L, hexane 0.1~1.0g/L; Solubility in water is 4mg/L. The distribution coefficient was 1700. It is stable to acid, alkali, light and heat, and 95% does not deteriorate within half a year at 30 ℃. |
2-(2-BENZOTHIAZOLYLOXY)-N-METHYLACETANILIDE - Risk and Safety
| Hazard Symbols | N - Dangerous for the environment |
| Risk Codes | 51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | 61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 |
| WGK Germany | 2 |
| RTECS | AB4542550 |
| HS Code | 29342000 |
| Toxicity | LD50 in rats, mice (mg/kg): >5000, >5000 orally; >1000, >1000 s.c.; >5000, >5000 dermally; LC50 (4 hr) in rats: 134 mg/m3 (Schmidt) |
2-(2-BENZOTHIAZOLYLOXY)-N-METHYLACETANILIDE - 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) |
| Overview | Mefenacet was first developed by Bayer, Germany, in 1987, it was put into production in Japan under the trade name Hinochloa, Rancho. In order to enhance the herbicide effect and adapt to the use of different regions and countries, some foreign companies have carried out research on the preparation. Mefenacetin is a kind of chemical herbicide, which is mainly used in transplanting paddy fields. It is an inhibitor of the growth and division of grass weed cells, which can effectively control grass weeds and has special effects on Humulus scandens, it also has control effect on annual weeds, cow felt, melon, Alisma orientalis and so on, and has excellent selectivity for transplanting rice field. Rice is a key crop in China. In order to ensure high yield of rice and improve its yield per unit area, the use of excellent chemical herbicides is a crucial means. |
| synthesis method | on the basis of literature summary and exploratory experiments, taking into account the source of raw materials, the yield, purity, process feasibility and environmental pollution and other factors, selected to N-methyl aniline, chloro ethyl phthalate chloride and Benzo Thio wave as main raw materials, through the reaction of chloro ethyl phthalate, lipidation reaction, synthesis of mefenesin by fat alcoholysis reaction and condensation reaction. The raw materials required by the synthesis route are easily available, the process is relatively simple, the intermediate process is easy to control, the discharge of the three wastes is small, and the industrial production is easy to realize. Figure 2 is the synthetic route of mefenacanthamide |
| dosage form | Single Dose: 4% granules. Mixture: mefenesin (3.5%)+ pyrazolide (6%) granules; Mefenesin (3.5%)+ pyrazolide (4%)+ butyryloxamide (4%) granules; Mefenozamide (3.5%)+ pyrazolide (4%)+ bentazon (5.5%) granules: mefenesin (5%)+ naphthylpropylamine (7%) granules; Mefenesin (3.5%)+ bensulfuron (0.17%) granules; mefenacetamide (4%)+ bensulfuron (0.25%) granules. |
| mode of action, mechanism | This agent is a kind of acyl aniline herbicide, which is an inhibitor of cell growth and division. It has a particularly strong inhibitory effect on the division of the mother cell. It was observed that the medicament acts at the growing point of the plant in the stationary phase and the metabolic phase of the cell propagation cycle, and inhibits the growth of Humulus scandens until death by inhibiting cell division and enlargement. The appearance of the medicinal herb was: abnormal hypertrophy of the growing point of the stem and leaf and root, the leaf sheath and leaf body became thick green, the growth of the plant was inhibited, and the stem and leaf became yellow and died. The withering time of Humulus scandens was prolonged with the increase of leaf age. |
| control object | This product is mainly used for transplanting paddy field, which can effectively control grass weeds and has special effects on Humulus scandens, humulus scandens could be killed from pre-occurrence to 3-leaf stage. It also has good control effect on cow felt, Alisma orientalis, duck tongue grass, node vegetables, atypical Cyperus papyrifera, semisanthus orientalis and perennial water papyrifera. |
| Usage | in transplanting paddy field, 3~10 days after transplanting (Humulus scandens 2 leaf period), 3 to 14 days (Humulus scandens 3 leaves or 3.5 leaf stage), spraying method for irrigation. Dosage: 4% mefenesin granules 2~2.7/mu. The effective dose of Humulus scandens, depending on the age of the leaf size: 1.5 leaves, 2.5 leaves, 3.5 leaves, 4 leaves were 33 grams of active ingredients, 67 grams, 100 grams, 133g/mu. The maintenance time of the efficacy in the paddy field varies according to the dosage: 67g of active ingredient for 30 days, 100g for 50 days, 133g for 60 days. The water solubility of the agent is only 4 mg/l, with strong soil adsorption and less penetration. Under General paddy field conditions, most of the dosage is distributed within 1cm of the surface layer, forming a treatment layer, seedling growth should not be in contact with this layer. Mefenacet had excellent selectivity for transplanting rice. It can also be used to control weeds in dry fields with 50% mefenacao emulsifiable concentrate, and 8kg/ha is used as the surface treatment before weed bud, and it can be used for Humulus scandens, ascending horse Tang, broken rice papyrifera, garden vegetables, Portulaca oleracea, Chinese chestnut, good control effect. |
| toxicity | rat acute oral LD50>5000mg/kg; Acute percutaneous LD50>5000mg/kg; acute inhalation of lc500.02 mg/L (powder, 4H), the rats fed the test for 2 years without the effect of the dose of 100mg/kg. To carp lc508.0 mg/L (96H), rainbow trout lc508.0 mg/L (96H). |
| references | [1] Wu Lin. Study on the synthesis of mefenesin [D]. Harbin University of Science and Technology, 2006. [2] Wang Zhenrong, Edited by Li Buqing. A complete collection of pesticides. Beijing: China Commercial Press. 1996. Pages 628-630. [3] Zhu Yonghe, Wang Zhenrong, Li Buqing. Pesticides. Beijing: publishing center of agricultural science and education, Sanshan Publishing House, China. 2006. Page 702-704. |
| Use | cytogenesis and division inhibitor, low toxicity. It is mainly used to control Gramineae weeds, and high-activity scaly agent in paddy field, which can be killed before the occurrence of Humulus scandens to the three-leaf stage. It has control effect on annual weeds and oxirane. It has a good selectivity for transplanting rice, and has a quick effect before the occurrence to the early stage, and the effective period is more than 30d. The application method can be irrigation and spraying. mainly used in transplanting field and seedling-throwing field, which can effectively control grass weeds |
| production method | preparation of α-hydroxy-N-methylacetanilide anhydrous Glycolic acid is reacted with acetyl chloride at 20~30 ℃, excess acetyl chloride was distilled off at 90~100 ℃, after cooling, thionyl chloride was added dropwise, heated to boiling, reacted for 3H, and purified by distillation under reduced pressure to obtain acetoxyacetyl chloride in 70% yield, the reaction was carried out at 0~10 ℃ with N-methylaniline and continued at 20 ℃ for 15h to obtain acetoxy-N-methylacetoaniline in 74% yield; the product acetoxy-N-methylacetoaniline was dissolved in methanol, concentrated sodium hydroxide solution was added at 30 ℃, stirred at 20 ℃ for 15h, after work-up, pale yellow white crystalline α-hydroxy-N-methylacetoaniline was obtained in 86% yield. 2-chlorobenzothiazole can also be benzothiazole in the presence of AlCl3, POCl3, in pyridine solution by chlorine chlorination. Synthesis of mefensilate in the dissolved sodium hydroxide and α-hydroxy-N-methylacetoaniline, 2-chlorobenzothiazole was added at 20 ℃ and reacted at 40~50 ℃ for 2H, after post-treatment, fenaclopine, m. Et al. P. 118 °c, yield 84%. |
| category | pesticide |
| toxicity grade | high toxicity |
| Acute toxicity | oral-rat LD50:>5000 mg/kg; Inhalation-rat LC50: >94.5 mg/m3 |
| flammability hazard characteristics | flammability; Toxic nitrogen oxide and sulfur oxide fumes from combustion |
| storage and transportation characteristics | ventilation and low temperature drying; Separate storage |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, water mist |
Last Update：2024-04-09 19:05:14
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Multiple Specifications
Product Name: Mefenacet Visit Supplier Webpage Request for quotationCAS: 73250-68-7
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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