88349-88-6

Usage

Uses

Cloquintocet is a herbicidal composition that contains Pinoxaden(P469505).

InChI:InChI=1/C11H8ClNO3/c12-8-3-4-9(16-6-10(14)15)11-7(8)2-1-5-13-11/h1-5H,6H2,(H,14,15)

Upstream product

• 88349-90-0 ethyl ((5-chloroquinolin-8-yl)oxy)acetate 
• 130-16-5 5-Chloro-8-hydroxyquinoline 
• 79-11-8 chloroacetic acid 
• 99607-70-2 cloquintocet-mexyl 

Downstream Products

• 1346981-39-2 C₂₃H₁₆ClN₃O₃S 
• 1346981-41-6 C₂₄H₁₈ClN₃O₃S 
• 1346981-47-2 C₂₅H₁₈ClN₃O₃ 

Relevant academic research and scientific papers

Process Development for the Crop Safener Cloquintocet Acid

A practical one-pot process was developed for (5-chloroquinolin-8-yloxy)acetic acid (CQC acid), known commercially as cloquintocet, a crop safener that is added to various herbicide formulations to reduce crop damage. The process consists of (1) conversion of 5-chloro-8-hydroxyquinoline (5-ChQ) to its corresponding sodium salt 5-ChQ-Na with 50 wt % NaOH in dimethyl sulfoxide (DMSO), (2) alkylation of 5-ChQ-Na with methyl 2-chloroacetate to generate CQC methyl ester (CQC-Me) after removal of water by distillation under reduced pressure, and (3) hydrolysis of CQC-Me with a catalytic amount of 0.1 N HCl (0.5 mol %) or 0.1 N H2SO4 (0.25 mol %) to afford CQC acid in >90% yield with >98% purity. All of the steps were carried out in one pot with only one isolation. Recovery and reuse of DMSO were also demonstrated. Each step/stage of the process was subjected to reactive chemical evaluation by differential scanning calorimetry and/or accelerating rate calorimetry for identification of potential safety hazards.

Synthesis method of cloquintocet-mexyl

The invention discloses a cloquintocet-mexyl synthesis method which comprises the following steps: (1) preparing methyl 5-chloro-8-quinolinoxyacetate by taking 5-chloro-8-hydroxyquinoline and methyl chloroacetate as raw materials, DMF (Dimethyl Formamide) as a solvent and potassium carbonate as an acid-binding agent; (2) carrying out alkaline hydrolysis on the methyl 5-chloro-8-quinolinoxyacetate prepared in the step (1), and then carrying out acid precipitation to prepare 5-chloro-8-quinolinoxyacetic acid; and (3) carrying out esterification reaction on the 5-chloro-8-quinolinoxyacetic acid prepared in the step (2) and 2-heptanol to prepare cloquintocet-mexyl. On the basis of an existing common industrial process, the prepared methyl 5-chloro-8-quinolinoxyacetate is hydrolyzed into 5-chloro-8-quinolinoxyacetic acid and then esterification reaction is conducted on the 5-chloro-8-quinolinoxyacetic acid and 2-heptanol to prepare cloquintocet-mexyl. The product yield is improved, the process is simple, and industrial production is easy.

PROCESS FOR THE PREPARATION OF A QUINOLINE CARBOXYLIC ACID

The invention provides a process for the preparation of a carboxylic acid of formula (IV) (which is useful as a safener for herbicides): wherein R1 is hydrogen or chlorine, comprising the steps of: (i) subjecting a compound of formula (V) wherein: R1 is as defmed above; and R2 is C1-C18 alkyl; C1-C6 alkoxyC1-C8 alkyl-; optionally substituted phenyl; or optionally substituted benzyl; to hydrolysis under acidic conditions to give a solution of a quinolinium salt; and (ii) addingbase to the solution obtained in step (i) to give the free carboxylic acid (IV). The invention also provides a solid (e.g. particulate) form of one quinoline carboxylic acid compound within formula (IV) defmed by R1 being chlorine;and novel intermediates useable in the above process.

PROCESS FOR THE PREPARATION OF A QUINOLINE CARBOXYLIC ACID

Process for the preparation of a quinoline carboxylic acid The invention provides a process for the preparation of a carboxylic acid of formula (IV) (which is useful as a safener for herbicides): wherein R1 is hydrogen or chlorine, comprising the steps of: (i) subjecting a compound of formula (V) wherein: R1 is as defined above;and R2 is C1-C18 alkyl;C1-C6 alkoxyC1-C8 alkyl-;optionally substituted phenyl; or optionally substituted benzyl; to hydrolysis under acidic conditions to give a solution of a quinolinium salt;and (ii) addingbase to the solution obtained in step (i) to give the free carboxylic acid (IV). The invention also provides a solid (e.g. particulate) form of one quinoline carboxylic acid compound within formula (IV) defined by R1 being chlorine;and novel intermediates useable in the above process.

Synthesis and antimicrobial activities of novel 8-(1-alkyl//alkylsulphonyl/ alkoxycarbonyl-benzimidazol-2-ylmethoxy)-5-chloroquinolines

The synthesis of a series of novel 8-(1-alkyl/alkylsulphonyl/ alkoxycarbonyl-benzimidazol-2-ylmethoxy)-5-chloroquinoline derivatives is reported. These derivatives were prepared by the condensation of o-phenylenediamine with [(5-chloroquinolin-8-yl)oxy]ac

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.

Selective herbicidal compositions in the form of concentrated microemulsions

The invention relates to novel herbicidal compositions which comprise herbicidal active substances from the class of the phenoxyphenoxy- and heteroaryloxyphenoxy-carboxylic acid derivatives, a dispersant from the class of the fatty alcohol polyoxypropylene-polyoxyethylene ethers and/or the polyoxyethylene-polyoxypropylene block copolymers, emulsifier or wetting agent from the group comprising calcium dodecylbenzenesulfonate, fatty acid polyglycol esters, the ethoxylated nonylphenols and the alkanol polyglycol ethers, organic solvents and water, in the form of microemulsions which have low viscosity and are stable chemically and with regard to their technical properties in use. The invention furthermore relates to a process for preparing these microemulsions by stirring, shaking or static mixing. Prior to the biological application of these formulations, they are mixed with water and thus give spray mixtures which are perfect with regard to their technical properties in use.