81335-37-7

Usage

Uses

Agricultural chemical.

Pharmacology

Plant Metabolism. The selectivity of imazaquin is due to differential rates and routes of metabolism in tolerant crops versus susceptible weeds (3). The primary metabolite in soybeans is a pyrroloquinoline acetamide (41, Fig. 18), which is immobile in the plant and is not an inhibitor of acetolactate synthase. This metabolite is further broken down to eventually yield a dicarboxylic acid. Animal Metabolism. Metabolism studies in the rat showed that they rapidly excreted unchanged imazaquin in the urine (5). There was no accumulation of imazaquin or any of its derivatives in the liver, kidney, muscle, fat, or blood. There was no detectable residue in the liver, kidney, muscle, or fat of lactating goats and laying hens, which were fed imazaquin for 7 consecutive days (5).

Metabolism

Imazaquin 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. Imazaquin is rapidly absorbed through the roots of plants. Once it enters the plant, imazaquin 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.

Toxicity evaluation

Imazaquin 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/C17H17N3O3/c1-9(2)17(3)16(23)19-14(20-17)13-11(15(21)22)8-10-6-4-5-7-12(10)18-13/h4-9H,1-3H3,(H,21,22)(H,19,20,23)

Upstream product

• 13893-53-3 2-amino-2,3-dimethylbutyronitrile 
• 40963-14-2 2-amino-2,3-dimethylbutyramide 
• 32413-08-4 diethyl quinoline-2,3-dicarboxylate 

Relevant academic research and scientific papers

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.

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.

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.