81335-77-5

Basic information

• Product Name: Imazethapyr
• Synonyms: (+-)-midazol-2-yl)-5-ethyl;5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl)-5-ethyl-2-((+-)-3-pyridinecarboxylicaci;5-dihydro-4-methyl-4(1-methylethyl)-5-oxo-1h-imidazol-2yl)-5-ethyl-3-(+-)-2-(;ac263,499;(RS)-5-ETHYL-2-(4-ISOPROPYL-4-METHYL-5-OXO-2-IMIDAZOLIN-2-YL)-NICOTINIC ACID;PURSUIT;PURSUIT DG;PURSUIT(R)
• CAS NO: 81335-77-5
• Molecular Formula: C₁₅H₁₉N₃O₃
• Molecular Weight: 289.33
• Product Categories: HERBICIDE;HammerLabware;AMPCO;Labware;Tools
• Mol File: 81335-77-5.mol

Chemical Properties

• Melting Point: 169-173°C
• Boiling Point: 431.49°C (rough estimate)
• Flash Point: 224 °C
• Appearance: /
• Density: 1.1302 (rough estimate)
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: 0-6°C
• PKA: pK1 2.1; pK2 3.9(at 25℃)
• BRN: 7437150
• CAS DataBase Reference: Imazethapyr(CAS DataBase Reference)
• NIST Chemistry Reference: Imazethapyr(81335-77-5)
• EPA Substance Registry System: Imazethapyr(81335-77-5)

Safety Data

• WGK Germany: 1
• RTECS: US5682900
• Hazardous Substances Data: 81335-77-5(Hazardous Substances Data)

Usage

Uses

Used in Agroecosystems:
Imazethapyr is used as a herbicide in biological studies to evaluate its effect on non-target vegetation within agroecosystems.
Used in Soybean Crop Protection:
Imazethapyr is used as a selectively pre-emergence and early post-emergence soybean crop herbicide for effectively preventing the growth of various weeds such as amaranth, Polygonum, Abutilonum, Solanum, Xanthium, Setaria, and Crabgrass.
Used in Weed Control:
Imazethapyr is used as a herbicide for controlling many grasses and broad-leaved weeds. It can be applied through pre-mixing with soil for treatment before sowing, soil surface treatment before emergence, and early post-emergence application. It is effective against two-color sorghum, westerly, amaranth, mandala, barnyard grass, millet, setaria viridis, hemp, amaranthus retroflexus, and goosefoots.
Used in Legume Crop Protection:
Imazethapyr is selective for other legume crops at a dosage of 36-140g/hm2. It can be applied through soil treatment or early post-emergence spraying to control weeds effectively.
The herbicide works by being absorbed through the roots and leaves, conducting in the xylem and phloem, and accumulating in the plant meristem. It affects the biosynthesis of valine, leucine, and isoleucine, destroying the protein and killing the plant. Soybean has resistance to Imazethapyr, and the general application amount ranges from 140 to 280g/hm2.

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.

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.

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)

Upstream product

• 40963-14-2 2-amino-2,3-dimethylbutyramide 
• 202586-57-0 C₁₀H₁₁NO₄ 
• 102268-15-5 5-ethyl-2,3-pyridinedicarboxylic acid 
• 105151-39-1 diethyl 5-ethyl-2,3-pyridinedicarboxylate 
• 922-63-4 ethylacrolein 

Downstream Products

• 1304051-02-2 C₇H₆O₃*C₁₅H₁₉N₃O₃ 

Relevant articles and documents

Synthesis method of imazethapyr

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 of imazethapyr with stable crystal form

The embodiment of the invention provides a preparation method of imazethapyr with a stable crystal form. The preparation method comprises the following steps: adding an acid into an imazethapyr salinesolution containing a crystallization denaturant to separate out imazethapyr crystals, wherein the crystallization denaturant is benzene, alkylbenzene or halogenated alkane, and the preparation method disclosed by the invention is stable in crystal form, high in conversion rate and simple in preparation process.

Preparation method for imidazolinone compound

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.

Method for Controlling Rust Infections in Leguminous Plants

Method for controlling rust infections in leguminous plants by using heterocyclylcarboxanilides of the formula I where n=0-4; X=C1-C4-haloalkyl; Het=a pyrazole, thiazole or pyridine radical of the formula IIa, IIb or IIc where R1 is C1-C4-alkyl or C1-C4-haloalkyl, R2 is H or halogen, R3 is C1-C4-alkyl or C1-C4-haloalkyl, R4 is C1-C4-alkyl or C1-C4-haloalkyl and R5 is halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl or C1-C4-alkylsulfonyl, mixtures of heterocyclylcarboxanilides of the formula I and a fungicidally active compound II from the group of the azoles, acylalanines, amine derivatives, anilinopyrimidines, dicarboximides, dithiocarbamates, heterocylic compounds, phenylpyrroles, cinnamides, and analogs, or other fungicides according to the description, and also compositions and seed comprising these mixtures.

Formation of the imidazolinone ring under mild conditions in the presence of sodium hydride

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.

Synergistic herbicidal methods and compositions

The present invention provides a method for synergistic broad spectrum weed control which comprises applying to the weeds or their locus a synergistically effective amount of a combination of an imidazolinone herbicide plus (4-chloro-2-methylphenoxy)acetic acid (MCPA). Further provided are synergistic herbicidal compositions comprising an imidazolinone herbicide plus MCPA.

Herbicidal composition

The present invention relates to a herbicidal composition, comprising A) one or more compounds of the formula (I) 1in which Hal1 and Hal2 are identical or different halogen atoms, R1 is H, a cation or a C1-C20-carbon-containing radical and B) one or more surfactants, comprising as structural element at least 12 alkylene oxide units.

Herbicidal mixtures having a synergistic effect

PCT No. PCT/EP96/03996 Sec. 371 Date Feb. 17, 1998 Sec. 102(e) Date Feb. 17, 1998 PCT Filed Sep. 12, 1996 PCT Pub. No. WO97/10714 PCT Pub. Date Mar. 27, 1997A composition comprising at least one sulfonylurea of the formula I wherein R1 is substituted alkyl; halogen; a group ER6 (E=O, S or NR7); COOR8; NO2; S(O)oR9; SO2NR10R11; or CONR10R11; R2 is hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkoxy, haloalkyl, alkylsulfonyl, nitro, cyano or alkylthio; R3 is F, CF3, CF2Cl, CF2H, OCF3, OCF2Cl, or, if R1 is CO2CH3 and R2 is simultaneously fluorine, R3 is Cl, or, if R1 is CH2CF3 or CF2CF3, R3 is methyl, or, if R4 is OCF3 or OCF2Cl, R3 is OCF2H or OCF2Br; R4 is alkoxy, alkyl, alkylthio, alkylamino, dialkylamino, halogen, haloalkyl or haloalkoxy; and R5 is hydrogen, alkoxy or alkyl; or an enviromentally compatible salt of I, and an aryloxyalkanoic acid selected from the group consisting of 2,4-D, 2,4-DB, clomeprop, dichlorprop, dichlorprop-P, dichlorprop-P (2,4-DP-P), fenoprop (2,4,5-TP), fluoroxypyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napropanilide, triclopyr, and an enviromentally compatible salt thereof exhibits a synergistic herbicidal effect.

Substituted (hetero) aryl compounds, process for their preparation, agents containing them and their use as safeners

Substituted (hetero)aryl compounds, process for their preparation, agents containing them, and their use as safeners Compounds of the formula I and their salts, as defined in claim 1, are suitable as safeners for protecting crop plants against the phytotoxic side-effects of herbicides.

Method for safening herbicides in cereal crops using 5-aryloxy-1,2-(disubstituted)benzene compounds

There is provided a method for safening herbicides in cereal crop plants by using 5-aryloxy-1,2 -(disubstituted)benzene compounds of formula I STR1 Further provided are compositions comprising a 5-aryloxy-1,2-(disubstituted)benzene compound of formula I.