81335-77-5 Usage
Chemical Properties
Pure product: colorless crystals, no odor. m. p. 169-174 °C, vapor pressure: being less than 0.013 x 10-3 Pa (60 °C). Solubility at 25 ℃: Methanol 105g / L, Isopropyl alcohol 17g / L, Toluene 5g / L, Heptane 0.9g / L, Water 1.4g / L. Corrosive.
Herbicide
Imazethapyr is an organic heterocyclic herbicide which belongs to the class of imidazolinones.
Its isopropylamine salt is suitable for the control of all kinds of weed, having excellent herbicidal activity on sedge weeds, annual and perennial monocotyledonous weeds, broad-leaved weeds and miscellaneous wood. It can be used before or after buds, can be quickly absorbed by plant roots and leaves, being capable of inhibiting the biosynthesis of plant side chain amino acids (valine, leucine, and isoleucine), destroying the protein so that the growth of weeds is suppressed and weeds will finally die. Sensitive weeds immediately stop growing after foliar treatment, usually at 2 to 4 weeks after death. Selectivity is due to the different metabolic rate of plants, resistant plants metabolize faster than sensitive plants. Leguminous plants, after absorbance of Putex special, will quickly metabolize it. It is safe to soybean. Imazethapyr, inside the soybean body, has a half-life of about 1.6 days. In the dosage of above 100g active ingredient / hm2, it will have significant inhibitory effect on the soybean during initial stage of application, but the plant can quickly recover.
Be caution when used in low-lying fields and acid soil. The drug has a long residual period in the soil. Any sensitive crops such as Chinese cabbage, rape, cucumber, potato, eggplant, pepper, tomato, beet, watermelon and sorghum can not be planted within three years after application of imazethapyr. However, according to the recommended dose, the later crop can be spring wheat, soybeans or corn. In multiple cropping per year area of our country, it is even more important to choose rotated crop according to the specific circumstances.
Synthesis and screening of imidazolinones began in 1975, M. Los and others first reported such herbicides in 1982. In 1983, PLOrwick et al. reported that imazapyr and its imazapyr-isopropylammonium. Meanwhile, DL Shaner et al. reported imazaquin and its imazam-ammonium, making imidazolinone compounds an active area for the development of new herbicides. Then D. L. Shaner and N.E. Shafer reported the herbicidal activity of imazamethabez-methyl, and T. Malefyt et al reported the herbicidal activity of imazethapyr and its imazethapyr-ammonium.
Application
It belongs to imidazolinones selective pre-emergence and post-emergence herbicides, being the branched-chain amino acid synthesis inhibitors. It is absorbed through the roots and leaves and conducts in the xylem and phloem and accumulates in the plant meristem, affecting the biosynthesis of valine, leucine and isoleucine, destroying the protein and killing the plant. Pre-mixing it with soil for treatment before sowing, applying soil surface treatment before emergence and early post-emergence application can control many grasses and broad-leaved weeds. Soybean has resistance; the general amount is 140 ~ 280g / hm2; it has also been reported of using 75 ~ 100g / hm2 in soybean field for soil treatment. It is also selective for other legume at a dosage of 36 ~ 140g / hm2. If using a dose of 36 ~ 142 g/ hm2, either mixing with soil or early post-emergence spraying, can effectively control two-color sorghum, westerly, amaranth, mandala and so on; the dose of 100 ~ 125g / hm2, when mixed with soil or pre-treated before emergence, have excellent control effect on the barnyard grass, millet, setaria viridis, hemp, amaranthus retroflexus and goosefoots. Post-treatment can control annual grass weeds and broad-leaved weeds with the required dose of 200 ~ 250g / hm2.
Selectively pre-emergence and early post-emergence soybean crop herbicide, which can effectively prevent the amaranth, Polygonum, Abutilonum, Solanum, Xanthium, Setaria, Crabgrass and other weeds.
Preparation
Diketene is treated with chlorine in the dichloromethane to extract the chloroacetic acid ethyl ester. The compound is reacted with methylene chloride at room temperature for 10 hours to give 2, 4-dichloroacetoacetate. Reflux 2-ethylacrolein and ammonium sulfamate in absolute ethanol for 1.5 hours to give ethyl 2-chloromethyl-ethyl nicotinate, which is further reacted with 2-amino-2,3-bis Methyl butyramide and sodium bicarbonate in dimethyl sulfoxide at 80 ℃ for 6h, the resulting condensation product was hydrolyzed and then cyclized in acetic acid to produce imazethapyr.
2, 3-pyridinedicarboxylic acid is reacted with acetic anhydride in toluene to produce pyridine dianhydride, which is then reacted with (CH3) 2CHCOH3 (CN) NH2 at 10-12 ° C to form carbamoyl nicotinic acid. Apply hydrogen peroxide in sodium hydroxide solution for hydrolysis, and finally heat to 70 ℃ for cyclization reaction, that is, imazapyr.
Acute Toxicity
Oral - Rat LD50: 5000 mg / kg; Oral - Mouse LD50: 5000 mg / kg.
Flammability Hazard Characteristics
Combustion produces toxic nitrogen oxides
Storage and transportation
warehouse ventilated, low temperature, and dry; separate it from food raw materials for transportation.
Uses
Imazethapyr is a herbicide that that is used in biological studies to evaluate the effect on non-target vegetation within agroecosystems.
Check Digit Verification of cas no
The CAS Registry Mumber 81335-77-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,1,3,3 and 5 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 81335-77:
(7*8)+(6*1)+(5*3)+(4*3)+(3*5)+(2*7)+(1*7)=125
125 % 10 = 5
So 81335-77-5 is a valid CAS Registry Number.
InChI:InChI=1/C15H19N3O3/c1-5-9-6-10(13(19)20)11(16-7-9)12-17-14(21)15(4,18-12)8(2)3/h6-8H,5H2,1-4H3,(H,19,20)(H,17,18,21)
81335-77-5Relevant articles and documents
Synthesis method of imazethapyr
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, (2021/01/11)
The invention relates to a synthesis method of imazethapyr, wherein the synthesis method comprises the steps: by using 5-ethylpyridine-2,3-dicarboxylic acid as a raw material, reacting with acetic anhydride to generate 5-methylpyridine-2,3-dicarboxylic anhydride; and under a low-temperature condition, continuing to react with alcohol to generate a compound represented by a structural formula (I),carrying out ring closing reaction with 2-amino-2,3-dimethylbutyramide under an alkaline condition, extracting to regulate the pH value, and thus obtaining the imazapyr product. The method has the advantages that the method is high in route reaction speed, extremely high in product purity, high in yield, mild in reaction condition, free of isomers and few in three wastes, the synthesis process isextensive, the reaction condition is optimized, the equipment cost of the reaction is reduced, the produced product is easy to separate, and the production process is simplified. The structural formula (I) is described in the specification.
Preparation method for imidazolinone compound
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, (2019/03/29)
The invention provides a preparation method for an imidazolinone compound, belongs to the technical field of organic synthesis, and can solve the problems that a large amount of wastewater is producedand the content of impurities in the product is high in the existing process for preparing the imidazolinone compound. According to the preparation method for the imidazolinone compound provided by the invention, a solution of 5-alkyl pyridine-2,3-phthalate is synthesized from ammonium carbonate; the steps of adding water, extracting, refining and the like are avoided in post-treatment; the obtained solution of the 5-alkyl pyridine-2,3-phthalate is used for subsequent reaction; and the wastewater is not produced. Then, a catalyst is added in the process of preparing 5-alkyl pyridine-2,3-dimethylbenzene anhydride, and the pH is controlled in the subsequent reaction process, so that the production of the impurities can be avoided, and the product purity is improved. The imidazolinone compound prepared by the method provided by the invention can be used as a high-efficiency herbicide.
Formation of the imidazolinone ring under mild conditions in the presence of sodium hydride
Vasiliev, Aleksey N.,Lopez, Antonio F.,Fernandez, Julio D.,Mocchi, Anibal J.
, p. 535 - 540 (2007/10/03)
Substituted imidazolinones containing heterocyclic carboxylic acids as substituents and possessing herbicidal properties were synthesized by cyclization of 2-amino-2,3-dimethylbutyramide with heterocyclic ethyl dicarboxylates under mild conditions. The use of NaH as base leads to a significant increase in the reaction rate and allows the preparation of the target compounds in high yields.
