BUTATAF
Machette
CAS: 23184-66-9
Molecular Formula: C17H26ClNO2
BUTATAF - Names and Identifiers
| Name | Machette |
| Synonyms | TRAPP MACHETE Lambast BUTATAF Machette PARAGRAS CP 53619 Pillarset Butachlor pillarset DHANUCHLOR Hiltachlor MACHETE(R) FARMACHLOR RASAYANCHLOR Rasayanchlor N-(BUTOXYMETHYL)-2-CHLORO-2',6'-DIETHYLACETANILIDE N-(Butoxymethyl)-2-chloro-2',6'-diethylacetanilide 2-Chloro-2',6'-diethyl-N-(butoxymethyl) acetanilide n-(butoxymethyl)-2-chloro-n-(2,6-diethylphenyl)acetamide N-(Butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide n-(butoxymethyl)-2-chloro-n-(2,6-diethylphenyl)-acetamid N-(butoxymethyl)-2,2-dichloro-N-(2,6-diethylphenyl)acetamide |
| CAS | 23184-66-9 |
| EINECS | 245-477-8 |
| InChI | InChI=1/C17H25Cl2NO2/c1-4-7-11-22-12-20(17(21)16(18)19)15-13(5-2)9-8-10-14(15)6-3/h8-10,16H,4-7,11-12H2,1-3H3 |
BUTATAF - Physico-chemical Properties
| Molecular Formula | C17H26ClNO2 |
| Molar Mass | 311.85 |
| Density | d430 1.0695 |
| Melting Point | <-5°C |
| Boling Point | 156°C (0.5 torr) |
| Flash Point | 100°C |
| Water Solubility | 20mg/L(20 ºC) |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | Liquid |
| Color | Light yellow-purple |
| BRN | 2873811 |
| pKa | 1.20±0.50(Predicted) |
| Storage Condition | 0-6°C |
| Refractive Index | 1.5388 (estimate) |
| Physical and Chemical Properties | Melting point <-5°C boiling point 156°C (0.5 torr) |
| Use | It is a kind of high-efficiency and low-toxicity herbicide before germination, mainly used for controlling most annual gramineae and some dicotyledonous weeds in dryland crops |
BUTATAF - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN3082 9/PG 3 |
| WGK Germany | 3 |
| RTECS | AE1200000 |
| Toxicity | LD50 orally in rats: 1740 mg/kg (Strateva) |
BUTATAF - Upstream Downstream Industry
| Raw Materials | 2,6-Diethylaniline Formaldehyde Sodium hydroxide Phosphorus oxychloride Chloroacetic acid 1-Butanol |
BUTATAF - Nature
Open Data Verified Data
pure product is light yellow oily liquid. Soluble in acetone, ethanol, methanol, benzene and other organic solvents, solubility in water (20 deg C) 20mg/L. The light resistance was good, and the thermal decomposition was started at 275 °c.
Last Update：2025-06-10 22:55:16
BUTATAF - Preparation Method
Open Data Verified Data
N-methylene -2,6-= ethyl aniline was prepared by the reaction of 2,6-= ethyl aniline and paraformaldehyde, and then reacted with Chloroacetyl Chloride to form N-(2,6-= ethylphenyl)-N-chloromethylchloroacetamide and finally N-butanol to give butachlor.
Last Update：2022-01-01 10:12:41
BUTATAF - Application
Open Data Verified Data
It is a selective pre-emergence herbicide, which inhibits the synthesis of protein and kills weeds through the absorption of young shoots and young secondary roots. It is mainly used to control annual grass weeds, annual Cyperaceae weeds and some annual Broad-leaved weeds in rice fields, and also used to control weeds in barley, wheat, cotton and peanut crop fields.
Last Update：2025-08-19 16:24:40
BUTATAF - Safety
Open Data Verified Data
rat oral LD50:1740 mg/kg.
Last Update：2022-01-01 10:12:42
BUTATAF - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| herbicide | butachlor is a kind of amide internal absorption conduction type selective pre-bud herbicide, also known as anachlor, marchet, and herbicide. The pure product is a light yellow oily liquid with a slightly aromatic taste. Insoluble in water, easily soluble in a variety of organic solvents. The chemical properties are stable at room temperature and under neutral and weak alkaline conditions. Under strong acid conditions, it will accelerate its decomposition and can be degraded in soil. Low toxicity to humans and animals, stimulating skin and eyes, and high toxicity to fish. It is absorbed mainly by weedy shoots, followed by roots. After the plant absorbs butachlor, it inhibits and destroys protease in the body, affects the formation of protein, inhibits the normal growth and development of weed buds and young roots, thus causing weeds to die. butachlor is effective for weeds before germination and 2-leaf stage. It is suitable for controlling 1-year-old gramineous weeds such as barnyard grass, irregular sedge, broken rice sedge, thousand gold, and cow king grass in rice fields. It can also be used to control weeds such as winter barley, wheat to control hard grasses, kanmai Niang, ducktongue, johngrass, valvular flower, firefly, and clavicle, but it is good for water three-sided, cross-stalked, wild Cigu, etc. Perennial weeds have no obvious control effect. When used on clay loam and soil with high organic matter content, the agent can be absorbed by soil colloid, is not easy to be leached, and the effective period can reach 1-2 months. |
| mechanism of action | butachlor is generally used as a sealing agent for paddy fields, or used before the first leaf stage of weeds to exert ideal efficacy. After the use of the agent, butachlor is absorbed by the weed buds, and then transmitted to various parts of the weed to play a role. The absorbed butachlor will inhibit and destroy the production of protease in the weed body, affect the synthesis of weed protein, and cause the weed buds and roots to fail to grow and develop normally, resulting in the death of weeds. When butachlor is applied in dry land, it is necessary to ensure that the soil is moist, otherwise it is easy to cause phytotoxicity. |
| phytotoxicity | only a small amount of butachlor can be absorbed by rice seedlings after application, and it is rapidly and completely decomposed and metabolized in the body, thus rice seedlings have strong drug resistance. However, in the case of excessive dosage, it will cause phytotoxicity to rice seedlings, resulting in symptoms such as growth inhibition and root enlargement, and in severe cases, it will lead to dead seedlings. For transplanting rice fields and direct seeding rice fields, the pure medicinal amount per mu should not exceed 90 grams, otherwise it will cause phytotoxicity to rice seedlings. The symptoms of butachlor phytotoxicity can be divided into three types: mild, moderate and severe: The mild phytotoxicity is manifested by mild dwarf of the plant and slightly faded green of the leaf color. Moderate phytotoxicity is characterized by dwarf plant shrinkage, obvious chlorosis of leaf color and inhibition of tillering. Severe phytotoxicity is characterized by dwarf plant, twisted heart leaves or no heart leaves, deep color of leaves, dark green, no tillers, yellow rice roots, inhibition of new root growth, and dead seedlings in severe cases. Generally speaking, indica rice is more important than glutinous rice, and seedling throwing fields are more important than transplanting fields. From the perspective of the effect of phytotoxicity on rice growth and yield, mild phytotoxicity has no obvious effect on rice growth and yield. Moderate and severe phytotoxicity inhibit rice growth, dwarf plants and stop tillering, thus having a greater impact on yield. aiming at the causes of phytotoxicity caused by butachlor, the application amount is too large, the application amount is uneven, the field water layer is too deep during application, and the rice heart leaves are submerged. when applying, we should strictly control the dosage to apply evenly. when applying, we should keep a suitable water layer (3-5cm) in the field, and avoid flooding the heart leaves of rice or cutting off water. Once there is a phytotoxicity in the field, it can be washed with clear water for many times, the original field water is replaced, and quick-acting fertilizers such as potassium dihydrogen phosphate are applied to alleviate the phytotoxicity. |
| usage | dosage form: 60% butachlor emulsifiable concentrate application in dry fields requires application under soil wetting. It can prevent and remove annual gramineous weeds such as barnyard grass, horse tangcao, Setaria, Cow hair grass, ducktongue grass, jodgrass, and some dicotyledonous weeds. It is suitable for weeding cabbage, bean, radish, cabbage, eggplant, spinach and other vegetable fields. 1. weeding in direct seeding vegetable fields such as kidney beans, cowpea, pakchoi, fennel, cabbage, spinach, etc., use 100 ml per mu before sowing, add 40-50kg of water, spray the border surface evenly, and then sow. 2, cauliflower, cabbage, eggplant, sweet (spicy) pepper, tomato and other transplanting fields, with 150 grams per mu before planting, mixed with 50kg of water, evenly spray the soil. 3. use of rice seedling field and direct seeding field: after the field is finished, 2-3 days before sowing, shallow water layer is irrigated, 75-100ml per mu is used, 35kg of water is applied, the surface of the land is evenly sprayed, the water layer is kept for 2-3 days, and the water layer is drained for sowing. It can also spray 30kg of water with 100-125 ml per mu from 1 leaf to 2 leaf stage of seedlings and before 2 leaf stages of barnyard grass. After spraying, shallow water will not flood the heart leaves of seedlings and keep the water layer for 3-4 days. Early live broadcast field can be "soaked in head water" after sowing. 4, transplanting field use: generally 3-5 days after transplanting, barnyard grass and other germination peak, 100-125 ml per mu, 35kg of water evenly spray, or 5% granule 1000-1200g per mu, keep shallow water layer for 3-4 days. 5, dry land crop use: after sowing winter small (large) wheat and before emergence, 100-125 ml per mu and 50kg of water are evenly sprayed on the surface of the land. |
| precautions | (l) after applying pesticide and sowing in seedling field and direct seeding field, do not flood the field surface. (2) it has good control effect on weeds before excavation and poor control effect on large grass. pesticide should be applied as far as possible before sowing and planting. (3) Use medicine after seedlings. The water layer cannot flood the heart leaves of seedlings. In case of heavy rain, drain water in time. Otherwise, it is easy to cause drug damage. (4) butachlor is highly toxic to fish and cannot be used in fish farming rice fields. Do not pour residual medicine or water from sprayers into lakes, rivers or ponds. (5) butachlor is effective when the soil has a certain temperature. Dry fields should be watered or sprayed before application to improve the efficacy. (6) the sowing date of melons and solanaceous vegetables, the use of this product has certain phytotoxicity, and should be careful when applying it. (7) butachlor mainly kills monocotyledonous weeds, which is ineffective or has little effect on most broad-leaved weeds. For plots with more broad-leaved weeds in vegetable fields, consider using herbicides such as Ketlanin and dichloropyridyl acid. (8) spraying should be uniform to prevent excessive local medication from causing drug damage or leakage. |
| toxicity | acute oral LD50 in rats is 3300 mg/kg, acute percutaneous LD504080mg in rabbits/kg; The non-effective dose of rats fed for 3 months is 68~72 mg/kg, and that of mice is 123~278 mg/kg. No carcinogenic, teratogenic and mutagenic effects were found in animal experiments, and the accumulation was weak. Carp LC50 is 0.81mg/L (48h), 0.32mg/L (96h), blue gill LC50 is 0.44mg/L (96h). Bee oral LD50>100 μg/bee. Slight irritation to eyes and skin. |
| use | is a selective pre-bud herbicide, which inhibits protein synthesis and kills weeds through absorption of young buds and young secondary roots. It is mainly used in rice fields to control annual gramineous weeds and annual Cyperaceae weeds, and certain annual broad-leaved weeds. It can also be used for weed control in barley, wheat, cotton, and peanut crop fields. For example, 10~30g of active ingredients/100 m2 is used to control weeds such as barnyard grass, shallot, firefly, beef felt, joint grass, duck tongue grass, etc. 60% EC 6.8g/100 m2 was used 2~3 days before sowing in rice seedling field. Winter wheat and barley after sowing and covering soil, combined with irrigation and emergence water or rainfall, under the condition of good soil moisture, use 60% emulsifiable concentrate 15~18.8mL/100 m2 to spray the soil surface evenly. It is a high-efficiency and low-toxicity pre-bud herbicide, which is mainly used to control most annual gramineous and some dicotyledonous weeds in dryland crops It is used to control barnyard grass, cattle hair grass, duck tongue grass and other weeds in rice It is used to control gramineous weeds and annual broadleaf weeds in rice fields Selective pre-bud herbicide. Annual gramineous weeds and some broadleaf weeds mainly used for direct seeding or transplanting of rice fields. It is also selective for wheat, barley, sugar beet, cotton, peanut and cabbage crops. The effective dose is 1.0-4.5kg per hectare (active ingredient). Generally, it is soil surface treatment before budding and can also be applied after paddy field seedlings. It is an important variety of herbicides in paddy fields. It is mainly used for direct seeding or transplanting of rice fields to control annual gramineous weeds and some broadleaf weeds. It is also selective for wheat, barley, sugar beet, cotton, peanut and cabbage crops. The effective dose is 1.0-4.5kg per hectare (active ingredient). Generally, it is soil surface treatment before budding and can also be applied after paddy field seedlings. It is an important variety of herbicides in paddy fields. Calibration instruments and devices; evaluation methods; working standards; quality assurance/quality control; other. |
| production method | ① N-methylene -2, 6-diethylaniline is prepared by the reaction of DEA and paraformaldehyde, and then reacts with chloroacetyl chloride to generate N-(2, 6-diethylphenyl)-N-chloromethyl chloroacetamide and finally reacts with n-butanol to obtain butachlor; the reaction is the same as the preparation process of tolachlor, only the raw materials are polyoxymethylene and n-butanol respectively; ②DEA acylates with chloroacetic acid and phosphorus oxychloride to generate N-(2, 6-diethylphenyl) chloroacetamide, paraformaldehyde and hydrochloric acid, n-butanol undergoes etherification reaction to generate chloromethyl n-butyl ether, and then with N-(2, 6-diethylphenyl) chloroacetamide in the presence of sodium hydroxide to generate butachlor crude product, which is separated to obtain the finished product. Acetic acid loses water to form ketene, and chlorinated to form α-chloroacetyl chloride; aniline and ethylene react to introduce two ethyl groups at the ortho position of the amino group, and then interact with formaldehyde to form carbon-nitrogen double bonds; the last two The intermediate is added and reacts with n-butanol to produce butachlor. See "Pesticide" magazine 2002 issue 7 butachlor synthesis process improvement. |
| category | pesticide |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 1740 mg/kg |
| flammability hazard characteristics | 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 21:04:16
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Raw Materials for BUTATAF