5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid
Imazethapyr
CAS: 81335-77-5;81385-77-5
Molecular Formula: C15H19N3O3
5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid - Names and Identifiers
5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid - Physico-chemical Properties
| Molecular Formula | C15H19N3O3 |
| Molar Mass | 289.33 |
| Density | 1.1302 (rough estimate) |
| Melting Point | 169-173°C |
| Boling Point | 431.49°C (rough estimate) |
| Solubility | Solubility at 25°C: methanol 105g/L, isopropanol 17g/L, toluene 5g/L, heptane 0.9g/L, water 1.4g/L. |
| Appearance | Colorless crystals |
| BRN | 7437150 |
| pKa | pK1 2.1; pK2 3.9(at 25℃) |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.5600 (estimate) |
| Physical and Chemical Properties | Melting point 169-173°C pure colorless crystals, no smell. m. P. 169-174 °c, vapor pressure less than 0.013 x 10-3Pa (60 °c). Solubility at 25 ° C: methanol 105g/L, isopropanol 17g/L, toluene 5g/L, heptane 0.9g/L, water 1.4g/L. Corrosive. |
| Use | Selective pre-emergence and early post-emergence soybean field herbicide, can effectively control the amaranth, Polygonum, hemp, Solanum nigrum, Xanthium sibiricum, dog tail grass, Horse Tang and other gramineous weeds |
5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid - Risk and Safety
| WGK Germany | 1 |
| RTECS | US5682900 |
| HS Code | 29333990 |
| Toxicity | LD50 orally in rats and mice: >5000 mg/kg; dermally in rabbits: >2000 mg/kg (Peoples) |
5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| herbicide | Nicotiana tabacum is an organic heterocyclic herbicide, which belongs to Imidazolinone compounds, also known as pufende, imidazolidinoid acid, bezoar, pushen, and turfgrass tobacco, isopropylamine salts of which are suitable for the control of all weeds, against Cyperaceae weeds, annual and perennial monocotyledonous weeds, broadleaved weeds and miscellaneous trees have excellent herbicidal activity, can be used before or after Bud, can be quickly absorbed by plant roots and leaves, inhibit plant side chain amino acids (valine, leucine, isoleucine) the Biological synthesis, the destruction of protein, so that weed growth is inhibited, promote its death. Sensitive weeds stopped growing immediately after foliar treatment, and generally died after 2 to 4 weeks. The selectivity is due to the difference of the metabolic rate of plants, and the metabolic rate of resistant plants is faster than that of sensitive plants. After the absorption of the legume plant, it is quickly metabolized and decomposed in the body, and it is safe for soybean. The Half-Life of tobacco in soybean is about 1.6 days. When the dosage was above 100g/hm2, the growth of soybean was obviously inhibited at the initial stage of application, but it could recover quickly. it should be used with caution in low-lying field and acid soil. The residual effect of the drug in the soil is longer, the drug sensitive crops, such as cabbage, rape, cucumber, potato, eggplant, pepper, tomato, sugar beet, watermelon, sorghum and others could not be planted within three years of application of tobacco. But according to the recommended dose of treatment, after the crop can be spring wheat, soybean or corn. In China's more than one-year-old regions, More should be selected according to the specific circumstances of crop rotation. The synthesis and screening of Imidazolinone derivatives began in 1975 and 1982. Los et al. first reported such herbicides, 1983 p. L.Orwick et al. reported tobacco smoke (imazapyr) and its isopropylammonium salt (imazapyr-isopropylammonium), while D. L. Shaner et al. reported that imazaquin and its ammonium salt (imazaqin-ammonium) made Imidazolinone compounds an active area for the development of new herbicide varieties. Then D. L. Shaner and N.E.Shafer reports the herbicidal activity of imidazolyl ester (imazamethabez-methyl)[3], T. Et al. Malefyt et al. reported the herbicidal activity of imazetapyr and its ammonium salt (imazethapyr-ammonium). |
| toxicity | Acute oral LD50>5g/kg in rats, acute oral LD50>5g/kg in female mice, rabbit acute percutaneous LD50>2g/kg, slight irritation to the skin, the rabbit eye stimulation is reversible. Rats acute inhalation lc503.27 mg/L Air (analysis), 4.12mg/L Air (gravimetric method). No effect dose for feeding trials: Rats (2 years) and dogs (1 year)>10g/kg feed (highest test dose). Quail and wild duck acute oral LD50>2.15g/kg. Ames test showed that this product had no mutagenicity. Fish poisoning LC50(96 hours): 420mg/L blue gill, albitic 240mg/L, 340mg/L rainbow trout. Honey bee LD50>0.1mg head honey bee. Daphnia LC50(48 hours)<1g/L. This product is rapidly metabolized in rats, 24 hours after administration, 92% excreted by the urine, 5% fecal discharge; 48 hours after administration, in the blood, liver and kidney, residues in muscle and adipose tissue were less than 0.01mg/kg. [Sexual knowledge of tobacco toxicity] |
| preparation method | (1) diketene is treated with chlorine in dichloromethane to extract ethyl chloroacetoacetate, the reaction was carried out at room temperature for 10 hours to obtain ethyl 2, 4-dichloroacetoacetate, which was refluxed with 2-ethylacrolein and Ammonium sulfamate in anhydrous ethanol for 1.5 hours to obtain ethyl 2-chloromethyl-ethyl nicotinate, the latter is reacted with 2-amino -2, 3-dimethylbutanamide and sodium bicarbonate in dimethyl sulfoxide at 80 ° C. For 6h, and the resulting condensation product is hydrolyzed and then cyclized in acetic acid, that is to say, the product was made of tobacco. (2)2, 3-pyridinedicarboxylic acid reacts with acetic anhydride in toluene to form pyridine dianhydride, which then reacts with (CH3)2CHCOH3(CN). NH2 reacts at 10-12 °c to produce carbamoyl nicotinic acid, which is then hydrolyzed with hydrogen peroxide in an aqueous solution of sodium hydroxide, and finally heated to 70 °c to form a cyclization reaction. |
| Use | Imidazolinone selective pre-and early post-emergence herbicides, branched-chain amino acid synthesis inhibitors. Through the root and leaf absorption, and in the xylem and phloem conduction, accumulation in the plant meristem, affect the biosynthesis of valine, leucine, isoleucine, destruction of protein, so that plants are inhibited and died. Mixed soil treatment before sowing, soil surface treatment before emergence and early application after emergence. Many gramineae and broad-leaved weeds can be controlled, and soybean is tolerant, and the general dosage is 140~280g/hm2. It is also reported that 75~100g/hm2 is used for soil treatment in soybean field. It is also selective for other legume crops, and the dosage is 36~140g/hm2. Such as the use of 36~142g/hm2 dosage, whether mixed soil application or early application after Bud, can effectively control the two-color sorghum, the West Wind ancient, small amaranth, Datura and so on; with 100~125g/hm2 dose, before sowing mixed soil or Bud pretreatment, on Humulus scandens, millet, Green Dog Tail, hemp, amaranth, quinoa and so on have excellent control effect. The dose of post-emergence treatment was 200~250g/hm2 to control annual grass weeds and broad-leaved weeds. selective pre-emergence and early post-emergence soybean herbicide can effectively control amaranth, Polygonum, hemp, Solanum nigrum L., Xanthium sibiricum, grass weeds |
| production method | ethyl chloroacetoacetate is prepared by the interaction of diketene with chlorine and methyl chloride, and then with SO2Cl2, ethyl 2, 4-dichloroacetoacetate was obtained by chlorination; Ethyl 2, 4-dichloroacetoacetate was reacted with 2-ethylacrolein and Ammonium sulfamate to obtain ethyl 2-chloromethyl-ethyl nicotinate, 3-dimethylbutyramide is reacted and, upon hydrolysis, condensed to give imidazolinethanoic acid. |
| category | pesticide |
| toxicity grade | low toxicity |
| Acute toxicity | oral-rat LD50: 5000 mg/kg; Oral-mouse LD50: 5000 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 21:11:58
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Mobile: 86+15671228036
QQ: 2853786052
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Product Name: Imazethapyr Visit Supplier Webpage Request for quotationCAS: 81385-77-5
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Mobile: 18021002903
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