81334-34-1

Usage

Chemical Properties

solid

Uses

Imazapyr is an analytical standard used for proteomics research.

Pharmacology

Imazapyr kills plants by inhibiting acetolactate synthase (ALS) (I50 = 5 μM), which is the first common enzyme in the biosynthesis of the branched chain amino acids, valine, leucine, and isoleucine. Imazapyr is rapidly absorbed through the leaves of plants. Once it enters the plant, imazapyr rapidly 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

Imazapyr is weakly to moderately adsorbed on sandy loam and silt loam soils. The Freundlich adsorption coefficient ranges from 0 to 7.8 (15). Because imazapyr 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 bindsweakly 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 imazapyr in the soil is 25–142 d (14). Imazapyr remains in the top 30 cm of the soil with low leaching potential. The degradation route of imazapyr in the soil has not been determined.

Metabolism

Plant Metabolism. The selectivity of imazapyr is due to differential rates and routes of metabolism in tolerant crops versus susceptible weeds (3). The half-life of imazapyr in tolerant crops has not been accurately determined. The metabolic route of imazapyr is not clear. The parent compound can be metabolized to a tricyclic compound (33, Fig. 15) in some species, but the primary metabolite is an imidazopyrrolo-pyridine derivative (34, Fig. 15). Imazapyr acid does not inhibit acetolactate synthase, the target site for the imidazolinones, and it is immobile in the plant (4). Animal Metabolism. Metabolism studies in the rat showed that imazapyr is rapidly excreted in the urine (5). There was no accumulation of imazapyr or any of its derivatives in the liver, kidney, muscle, fat, or blood.

Toxicity evaluation

Imazapyr 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 in male rats.This herbicide also has a low potential for bioaccumulation in fish.

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

• 13893-53-3 2-amino-2,3-dimethylbutyronitrile 
• 98-98-6 2-Picolinic acid 
• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 
• 40963-14-2 2-amino-2,3-dimethylbutyramide 
• 81333-43-9 5,7-dihydro-alpha-isopropyl-alpha-methyl-5,7-dioxo-6H-pyrrolo[3,4-b]pyridine-6-acetamide 
• 24195-07-1 pyridine-2,3-dicarboxylic acid 2-methyl ester 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 161522-42-5 2-[(ethyloxy)carbonyl]-3-pyridinecarboxylic acid 
• 81334-62-5 5-isopropyl-5-methyl-2-(3-methyl-2-pyridyl)-2-imidazolin-4-one 
• 81333-51-9 methyl 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinate 
• 81333-51-9 Methyl 2-(isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinate 

Relevant academic research and scientific papers

HERBICIDAL COMPOSITIONS

The present invention provides compositions comprising herbicidally active compounds (A) and (B), where (A) represents one or more compounds of the general formula (I) or agrochemically compatible salts thereof [component (A)], and (B) represents one or more herbicides [component (B)]. The application further relates to a method and to the use of the herbicidal composition according to the invention for controlling harmful plants or for regulating growth.

Imazapyr acid intermediate as well as preparation method and application thereof

The invention discloses an imazapyr acid intermediate as well as a preparation method and application thereof. The imazapyr acid intermediate is obtained by taking pyridinyl-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. The imazapyr acid intermediate is further subjected to a ring closing reaction with an alkaline water solution, acidification is conducted by adding an acid to obtain imazapyr acid. The method is high in reaction speed, high in product purity, high in yield,mild in reaction condition, less in three wastes and extensive in synthesis process, optimizes the reaction condition and reduces the equipment cost of the reaction, also the produced product is easyto separate, and the production process is simplified.

Synthesis method of imazapyracid

The invention relates to a synthesis method of imazapyracid, relates to a preparation method of a compound, and in particular, relates to a production and synthesis method of imazapyracid; the methodis characterized by comprising the steps: taking quinolinic acid as a raw material and reacting with acetic anhydride to generate 2,3-pyridine dicarboxylic anhydride; and under a low-temperature condition, continuously reacting with alcohol to generate a compound represented by a structural formula (I), carrying out a ring closing reaction with 2-amino-2,3-dimethylbutyramide under an alkaline condition, extracting to adjust the pH value, and thus obtaining the imazapyracid product. The method has the advantages that a novel method for obtaining imazapyracid is provided, the route reaction speed is high, the product purity is extremely high, the yield is high, the reaction conditions are mild, isomers are avoided, catalysts are not needed, three wastes are few, the synthesis process is extensive, the reaction conditions are optimized, the reaction equipment cost is reduced, generated products are easy to separate, and the production process is simplified.

NOVEL CRYSTALLINE FORM OF IMAZAPYR, ITS PREPARATION AND USE

Provided is a crystalline form of imazapyr of formula (I), the crystal preparation process, the analyses of the crystal through various analytical methods and using the crystal to prepare the stable agrochemical for mulation. The use of various solvents towards the crystalline form preparation conditions is also provided.

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.

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.

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.

Super-spreading, low-foam surfactant for agricultural spray mixtures

Methods for preparing and applying agricultural sprays without undue foaming of the spray mixture employ a superspread-promoting, low foaming trisiloxane surfactant. Agricultural spray mixtures with super-spread properties, but limited foaming, comprise (A) a superspreading, low foaming trisiloxane surfactant and (B) an agricultural chemical spray mixture comprising water, an agricultural chemical (e.g., a pesticide), and optionally an organic surfactant, antifoam agent, and an organic solvent.