104098-48-8

Basic information

• Product Name: Imazameth
• Synonyms: (+/-)-2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl)-5-methyl-3-pyridinecarboxylic acid;IMAZAPIC;IMAZAMETH;Imazapic, Pestanal;2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-methylnicotinic acid;imazapic(bsi,iso);CADRE;IMAZAPI
• CAS NO: 104098-48-8
• Molecular Formula: C₁₄H₁₇N₃O₃
• Molecular Weight: 275.3
• Mol File: 104098-48-8.mol

Chemical Properties

• Boiling Point: 434.2 °C at 760 mmHg
• Flash Point: 216.4 °C
• Appearance: /
• Density: 1.318 g/cm³
• Vapor Pressure: 5.72E-10mmHg at 25°C
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly, Sonicated)
• PKA: 10.72±0.40(Predicted)
• CAS DataBase Reference: Imazameth(CAS DataBase Reference)
• NIST Chemistry Reference: Imazameth(104098-48-8)
• EPA Substance Registry System: Imazameth(104098-48-8)

Safety Data

• WGK Germany: 3
• RTECS: US7079100
• Hazardous Substances Data: 104098-48-8(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Imazameth is used as a herbicide for controlling a wide range of weeds in various crops, including peanuts, rangeland, sugarcane, and imidazolinone-resistant canola. It is particularly effective in providing maximum activity when used with a nonionic surfactant or oil adjuvant.
Used in Analytical and Biological Studies:
Imazameth is also utilized in the field of analytical and biological research, specifically for residue analysis and determination of imidazolinone herbicides in sunflower and soil samples. Gas chromatography-mass spectrometry (GC-MS) is a common technique employed for this purpose, allowing for accurate identification and quantification of the herbicide in various environmental and biological matrices.

Pharmacology

Imazapic kills plants by inhibiting acetolactate synthase (ALS) (I50 = 1 μM), which is the first common enzyme in the biosynthesis of the branched chain amino acids, valine, leucine, and isoleucine. Imazapic is rapidly absorbed through the leaves of plants. Once it enters the plant, imazapic translocates to the growing points and growth ceases within 1 day after herbicide application followed by chlorosis and then necrosis of the growing points. Total plant death will occur within 2 to 3 weeks after treatment.

Environmental Fate

Imazapic is weakly to moderately adsorbed on sandy loam and silt loam soils. The Freundlich adsorption coefficient ranges from 0.17 to 2.99, (12). Because imazapic is a weak acid and exists in different ionic states, soil pH has an effect on soil binding properties. The anionic form predominates at soil pH as low as 5.5, and this form binds weakly to soil. The neutral or molecular form is important at soil pH from 4 to 6.5. This form binds to soil organic matter and clay. The cationic form is important at pH less than 4. Because the soil is a heterogeneous mixture of acid and base chemical groups, there may be sites within a particular soil that are 2 to 3 pH units higher or lower than the average pH. The cationic form will bind tightly to the lower pH components. Because of these interactions, small decreases in pH below 6 will result in large increases in binding. The half-life of imazapic in the soil is 106 d. Imazapic remains in the top 30 cm of the soil with low leaching potential. The degradation route of imazapic in the soil has not been determined.

Metabolism

Plant Metabolism. The selectivity of imazapic is due to differential rates and routes of metabolism in tolerant crops versus susceptible weeds(10). Imazapic has excellent selectivity in peanuts, but is not selective in soybeans. The difference in the tolerance of these two legumes is due to the different routes of metabolism of imazapic in the two crops. The primary metabolite in soybeans is an imidazopyrrolo-pyridine derivative, whereas in peanuts, the primary metabolite is the glucose conjugate of hydroxy-imazapic. Although the imidazopyrrolo-pyridine derivative formed in soybean is immobile and is not an inhibitor of acetolactate synthase, the rate of degradation of imazapic in soybeans is not rapid enough for selectivity (10). In imidazolinone-resistant crops, the primary mechanism of selectivity is due to an altered acetolactate synthase that is not inhibited by the imazapic (11). Animal Metabolism (12). Metabolism studies in the rat showed that imazapic is rapidly excreted in the urine. There was no accumulation of imazapic or any of its derivatives in the liver, kidney, muscle, fat, or blood.

Toxicity evaluation

Imazapic has shown no mutagenic or genotoxic activity in the Ames assay, mammalian cell gene mutation assay, in vitro chromosome aberration assay, in vitro unscheduled DNA synthesis (URS) assay, or the in vivo dominant lethal assay inmale rats. The acute toxicity and effects on wildlife and soil microflora of imazapic are shown in Table 6. This herbicide also has a low potential for bioaccumulation in fish.

InChI:InChI=1/C14H17N3O3.H3N/c1-7(2)14(4)13(20)16-11(17-14)10-9(12(18)19)5-8(3)6-15-10;/h5-7H,1-4H3,(H,18,19)(H,16,17,20);1H3

Upstream product

• 40963-14-2 2-amino-2,3-dimethylbutyramide 
• 53636-65-0 5-methyl-pyridine-2,3-dicarboxylic acid 
• 112110-16-4 5-methyl-2,3-pyridinedicarboxylic acid dimethyl ester 

Downstream Products

• 53636-65-0 5-methyl-pyridine-2,3-dicarboxylic acid 
• 957786-00-4 2-formyl-5-methylnicotinic acid 
• 957786-04-8 2-carbamoyl-5-methylnicotinic acid 
• 957786-05-9 2-carbamidoyl-5-methylnicotinic acid 
• 957786-01-5 4-isopropyl-2-(3-hydroxy-5-methylpyridin-2-yl)-4-methyl-1H-imidazol-5(4H)-one 
• 53636-27-4 3-methyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione 

Relevant articles and documents

Synthetic method of imazameth

The invention relates to a synthetic method of imazameth, wherein the synthetic method comprises the following steps: reacting 5-methylpyridine-2,3-dicarboxylic acid serving as a raw material 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 on the compound and 2-amino-2,3-dimethylbutyramide under an alkaline condition to generate imazameth sodium salt, extracting to regulate the pH value, and thus obtaining an imazameth product. The method has the advantage that a new method for obtaining imazameth is provided. The method is high in reaction speed, extremely high in product purity, high in yield, mild in reaction condition, free of isomers, free of catalysts and few in three wastes, the synthesis process is extensive, the reaction condition is optimized, the reaction equipment cost is reduced, the produced product is easy to separate, and the production process is simplified. The structural formula (I) is described in the specification.

Imazameth intermediate as well as preparation method and application thereof

The invention discloses an imazameth intermediate as well as a preparation method and application thereof. The imazameth intermediate is obtained by taking 5-methylpyridinyl-2,3-dicarboxylic acid diethyl ester and 2-amino-2,3-dimethylbutanamide as raw materials through an amine ester exchange reaction under the action of a metal catalyst. Further a ring closing reaction is conducted with an alkaline aqueous solution, and an acid is added for acidification, so that imazamox is obtained. The method is high in reaction speed, high in product purity, high in yield, mild in reaction condition, lessin three wastes and extensive in synthesis process, optimizes the reaction condition and reduces the equipment cost of the reaction, also the produced product is easy to separate, and the productionprocess is simplified.

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.

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.

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.

Mixtures of herbicides and antidotes, (hetero)-aryloxy compounds, their preparation, compositions containing them, and their use

The invention relates to crop protection agents which comprise an active substance combination of herbicide and safener. The herbicides are selected from the group comprising the ALS inhibitors (ALS=acetolactate synthase) such as sulfonylureas, imidazolines, triazolopyrimidinesulfonamides, pyrimidyloxypyridinecarboxylic acid derivatives and pyrimidyloxybenzoic acid derivatives. The safeners are compounds of the formula I STR1 which are as defined in claim 1, where Z and Y are N or CH, it being possible for H to be replaced by X, X is H, Hal, haloalkyl or -alkoxy, alkyl, alkoxy, alkylthio, NO2, NH2, CN, alkylsulfonyl, A is alkylene or alkenylene, B is carboxyl or a derivative of the carboxyl group. The mixtures are mainly suitable for controlling harmful plants in the crops maize and cereals.

Substituted isoxazolines, process for their preparation, composition containing them, and their use of safeners

Substituted isoxazolines, process for their preparation, compositions containing them, and their use as safeners. Compounds of the formula (I) and salts thereof, STR1 in which R1 is carboxyl, formyl or another acyl radical or a derivative of the last-mentioned 3 groups, R2 is hydrogen, halogen, C1 -C18 -alkyl, C3 -C8 -cycloalkyl, C2 -C8 -alkenyl, C2 -C8 -alkynyl, C1 -C18 -alkoxy, C2 -C8 -alkenyloxy, C2 -C8 -alkynyloxy, C1 -C18 -alkylthio, C2 -C8 -alkenylthio, each of the last-mentioned 9 radicals in each case being unsubstituted or substituted, or (C1 -C8 -alkoxy)carbonyl, and R3 and R4 independently of one another are an aliphatic, araliphatic or heteroaraliphatic radical having 1 to 30 carbon atoms which is unsubstituted or substituted by one or more functional groups, or an aromatic or heteroaromatic radical which is unsubstituted or substituted, are suitable as safenets for pesticides, preferably herbicides, in crop plants. The compounds can be prepared from alkenes (II) and nitrile oxides (III) by the process of claim 6.

Methods for detecting acetohydroxyacid synthase inhibitors

The invention provides a method for determining whether a compound inhibits acetohydroxyacid synthase. The invention further provides a method for determining whether a plant is resistant to an acetohydroxyacid synthase inhibiting compound.