100646-51-3

Basic information

• Product Name: Quizalofop-p-ethyl
• Synonyms: 2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-,ethylester,(r)-propanoicaci;assureii;ethyl(r)-2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)propanoate;nci-861094;QUIZALOFOP-P-ETHYL;QUINOFOP-P-ETHYL;DPX-Y6202-31;ETHYL (R)-2-[4-(6-CHLORO-2-QUINOXALYLOXY)PHENOXY]PROPIONATE
• CAS NO: 100646-51-3
• Molecular Formula: C19H17ClN2O4
• Molecular Weight: 372.8
• Product Categories: INSECTICIDE;Aromatics;Chiral Reagents;Heterocycles;NULL;API
• Mol File: 100646-51-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 76-77°C
• Boiling Point: 503.9 °C at 760 mmHg
• Flash Point: >100 °C
• Appearance: White powder crystal
• Density: 1.301 g/cm³
• Vapor Pressure: 2.78E-10mmHg at 25°C
• Refractive Index: 1.604
• PKA: -1.39±0.48(Predicted)
• Water Solubility: 0.04 g/100 mL
• CAS DataBase Reference: Quizalofop-p-ethyl(CAS DataBase Reference)
• NIST Chemistry Reference: Quizalofop-p-ethyl(100646-51-3)
• EPA Substance Registry System: Quizalofop-p-ethyl(100646-51-3)

Safety Data

• Hazard Codes: Xn
• Statements: 21/22
• Safety Statements: 36/37
• RIDADR: UN3077 9/PG 3
• WGK Germany: 3
• RTECS: UA2458257
• Hazardous Substances Data: 100646-51-3(Hazardous Substances Data)

Usage

Uses

Post-emergence herbicide for control of grassy weeds in broad-leaved crops. Herbicide.

Purification Methods

This (±)-herbicide forms white crystals from Me2CO/EtOH and sublimes in vacuo. Large quantities can be distilled at high vacuum. Its solubilities at 20o in g/10mL are 0.09 (EtOH), 1.1 (Me2CO), 1.2 (xylene), 2.9 (*C6H6), and is nearly insoluble in H2O (0.3mg/L). The (±)-acid has [95977-28-9]. The R-ester enantiomer has m 76-77o (pale brown crystals from EtOH), [ ] D 20 + 3 5 . 9o (EtOH). It is the more active fatty acid synthase inhibitor (designated DPX-Y6202) used to control grassy weeds in broadleaf crops.

InChI:InChI=1/C19H17ClN2O4/c1-3-24-19(23)12(2)25-14-5-7-15(8-6-14)26-18-11-21-17-10-13(20)4-9-16(17)22-18/h4-12H,3H2,1-2H3/t12-/m1/s1

Upstream product

• 74497-15-7 (L) Ethyl 2-chloropropanoate 
• 76578-79-5 6-chloro-2-(4-hydroxyphenoxy)quinoxaline 
• 18671-97-1 2,6-dichloroquinoxaline 
• 64-17-5 ethanol 
• 94050-90-5 (R)-2-(4-hydroxyphenoxy)propionic acid 
• 57057-80-4 ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate 
• 123-31-9 hydroquinone 
• 33798-77-5 ethyl (S)-α-(4-methyl-phenylsulphonyloxy)-propionate 
• 76578-12-6 2-[4-(6-chloro-2-quinoxalyloxy)phenoxy]propionic acid 
• 687-47-8 (S)-Ethyl lactate 

Downstream Products

• 78104-59-3 D-2-[p-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propionic acid chloride 

Related news

Resistance Level and Metabolism of Barnyard-Grass (Echinochloa crusgalli (L.) Beauv.) Populations to Quizalofop-p-ethyl (cas 100646-51-3) in Heilongjiang Province, China08/12/2019

Eleven barnyardgrass populations were assayed. The highest resistant population was Geqiushan R with RI 125.45 resulted from the seed assay and 87.29 resulted from the whole plant bioassay followed by 853 R with RI 2.79 resulted from the seed assay and 6.04 resulted from the whole plant bioassay...detailed

Soaking seeds of winter rapeseed with Quizalofop-p-ethyl (cas 100646-51-3) alters plant growth and improves yield in a rice-rapeseed cropping system08/11/2019

Intercropping is an effective strategy to maximize production potential, profits, and land use efficiency. Sowing winter rapeseed in rice fields is a common cultivation technique in the Yangtze River basin in China, which is the world’s largest region for rapeseed production. However, the 10–1...detailed

A convenient method for determination of Quizalofop-p-ethyl (cas 100646-51-3) based on the fluorescence quenching of eosin Y in the presence of Pd(II)08/10/2019

A convenient fluorescence quenching method for determination of Quizalofop-p-ethyl(Qpe) was proposed in this paper. Eosin Y(EY) is a red dye with strong green fluorescence (λex/λem = 519/540 nm). The interaction between EY, Pd(II) and Qpe was investigated by fluorescence spectroscopy, resonanc...detailed

Potential Use of the Herbicide Quizalofop-p-ethyl (cas 100646-51-3) for Eicosapentaenoic Acid Overproduction by the Diatom Nitzschia laevis08/09/2019

The diatom Nitzschia laevis is a good alternative source of eicosapentaenoic acid (EPA). Besides strategies for high cell density culture, EPA productivity may be further improved by herbicides. The effect of the herbicide quizalofop-p-ethyl on the growth and EPA production is studied in this ar...detailed

Quizalofop-p-ethyl (cas 100646-51-3) exposure increases estrogen axis activity in male and slightly decreases estrogen axis activity in female zebrafish (Danio rerio)08/08/2019

The herbicide Quizalofop-P-ethyl (QpE) exerts toxic effects in fish, but limited information is currently available on its effects on the endocrine system. In the current study, adult zebrafish (Danio rerio) were exposed to different concentrations (0, 2, 20, 200 μg/L) of QpE for 30 days. In ma...detailed

A key esterase required for the mineralization of Quizalofop-p-ethyl (cas 100646-51-3) by a natural consortium of Rhodococcus sp. JT-3 and Brevundimonas sp. JT-908/07/2019

A natural consortium, named L1, of Rhodococcus sp. JT-3 and Brevundimonas sp. JT-9 was obtained from quizalofop-p-ethyl (QE) polluted soil. The consortium was able to use QE as a sole carbon source for growth and degraded 100 mg L−1 of QE in 60 h. Strain JT-3 initiated the catabolism of QE to qu...detailed

Comparison of transcriptome responses to glyphosate, isoxaflutole, Quizalofop-p-ethyl (cas 100646-51-3) and mesotrione in the HepaRG cell line08/06/2019

Use and thus exposure to quizalofop-p-ethyl, isoxaflutole, mesotrione and glyphosate, which are declared as active principles in commercial formulations of herbicides, is predicted to rapidly increase in coming years in an effort to overcome the wide-spread appearance of glyphosate-resistant wee...detailed

Relevant articles and documents

The enantioselective metabolic mechanism of quizalofop-ethyl and quizalofop-acid enantiomers in animal: Protein binding, intestinal absorption, and: In vitro metabolism in plasma and the microsome

To investigate the metabolic mechanism and enantioselectivity of the chiral herbicide quizalofop-ethyl and its primary chiral metabolite quizalofop-acid in animals by oral administration, the effects of the processes involved in digestion, absorption, tra

Synthesis method of quizalofop-P (by machine translation)

The invention belongs to the field of chemical engineering, and particularly relates to a synthetic method of quizalofop-methyl. To the invention, ethyl S-2 - ethyl chloropropionate is used instead S-2 - benzene sulfonic acid ethyl propionate, the esterification reaction step is omitted, the harsh reaction conditions and tedious post-treatment process are avoided, and meanwhile benzene sulfonate introduced by S-2 - benzenesulfonic acid ethyl propionate is avoided, and the environmental protection benefit of the process is improved. (by machine translation)

A method for producing quizalofop-P-ethyl environment-friendly process (by machine translation)

The present invention relates to a method for producing quizalofop-P-ethyl environment-friendly process, characterized in that the first hydroquinone with sodium hydroxide reaction to prepare the sodium salt of hydroquinone, with 2, 6 - dichloro quinozaline reaction, to obtain 4 - (6 - chloro - 2 kuikui oh linlin oxygen radical) phenol, then with paratoluene sulfonic acid ethyl lactate reaction to obtain the quizalofop-P-ethyl, herbicide then the grease of the alkaline hydrolysis, acidification, recovery 6 - chloro - 2 - hydroxy-quinoxaline. The synthesis process is advantageous in that the organic solvent in the reaction and post-processing, the system reduces the response of the alkaline, avoids the strong alkaline aqueous phase reactions the drawback of easy to produce impurities, reduces the raw material 2, 6 - dichloro quinozaline hydrolysis, so that the 4 - (6 - chloro - 2 kuikui oh linlin oxygen radical) to the phenol content of 98% or more, the yield of 92% or more, the recovery of the herbicide of the grease in the 6 - chloro - 2 - hydroxy-quinoxaline, not only reduces the discharge capacity of the solid waste, the protection of the environment, reduces the quizalofop-P-ethyl intermediate cost. (by machine translation)

A spore and intermediate 4 - (6 - chloro - 2 kuikui oh linlin oxygen radical) phenol synthesis method (by machine translation)

The invention relates to a synthesis method of spore, characterized in that the first hydroquinone with sodium hydroxide to prepare the sodium salt of hydroquinone, with 2, 6 - dichloro quinozaline reaction, to obtain 4 - (6 - chloro - 2 kuikui oh linlin oxygen radical) phenol, then with paratoluene sulfonic acid ethyl lactate reaction to obtain the spore. The synthesizing process to optimize the original process, advantage lies in the organic solvent in the reaction and post-processing, the system reduces the response of the alkaline, avoids the strong alkaline aqueous phase reactions the drawback of easy to produce impurities, reduces the raw material 2, 6 - dichloro quinozaline hydrolysis, so that the 4 - (6 - chloro - 2 kuikui oh linlin oxygen radical) to the phenol content of 98% or more, the yield of 92% or more, follow-up synthesis reaction the yield of 90% or more. (by machine translation)

Preparation method of quizalofop-P-ethyl

The invention provides a preparation method of quizalofop-P-ethyl. Ethyl S(-)-tosyllactate is prepared from p-toluenesulfonyl chloride and L-ethyl lactate through a reaction, and quizalofop-P-ethyl is prepared from ethyl S(-)-tosyllactate and 6-chloro-2-(4-hydroxyphenoxy) quinoxaline through a reaction. Ethyl S(-)-tosyllactate is prepared from liquid organic tertiary amine as alkali through reaction in a solvent-free and desiccant-free system, and hydrolysis of L-ethyl lactate is avoided, so that the content of impurities in p-toluenesulfonyl chloride is reduced, the content of impurities in quizalofop-P-ethyl is further reduced, and the chemical content of obtained quizalofop-P-ethyl is 98% or higher, the optical purity is high (R/S is larger than 99/1); operating procedures are simplified, and the production cost is reduced.

NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND

An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.

A Direct Approach to Enantiopure Propionate Derivatives from Ethyl Lactate

The S-propargyl xanthate derived from ethyl (S)-lactate reacts upon heating with various acidic substances to give the propionate transfer product in high yield and with complete inversion of configuration.

A method for preparing quizalofop

The invention belongs to the technical field of pesticide synthesis, and relates to a preparation method for quizalofop-p-ethyl, in particular to a preparation method for quizalofop-p-ethyl with R content of over 95 percent. The preparation method comprises the following steps of: preparing a chiral intermediate through monomolecular substitution reaction of L-ethyl lactate and paratoluensulfonyl chloride in an organic solvent by using two-step substitution reaction under the condition of excess chiral monomers; filtering to remove excess water absorbing agent and salt produced by reaction, washing excess L-ethyl lactate and acid-binding agent and distilling to remove the solvent; performing bimolecular substitution reaction on the chiral intermediate and 6-chloro-2-(4-hydroxyl phenoxyl) quinoxaline; and purifying to obtain R quizalofop-p-ethyl with high optical purity and stability, wherein the product yield and purity are high, the optical content is greater than 99 percent, R content reaches over 95 percent, and the yield is greater than 92 percent. The method has the advantages of simple process, easiness for control, short reaction period, long energy consumption and greatly reduced process cost.

A new method for one-pot synthesis of aryloxyphenoxypropionate herbicides using 2,4,6-trichloro-1,3,5-triazine and (n-BU)4NI as a homogeneous catalyst

The one-pot reaction of halo-heterocycle, (R)-4-hydroxyphenoxy propionic acid and an alcohol, amine or sulfonamide is described as an efficient method for the synthesis of aryloxyphenoxy propionate hrerbicides by using 2,4,6-trichloro-1,3,5-triazine in the presence of (n-BU) 4NI, as a homogeneous catalyst under mild conditions. The present procedure offers several advantages, such as good yields, short reaction times and easy workup.

PROCESS FOR PREPARING (R)-ARYLOXYPROPIONIC ACID ESTER DERIVATIVES

The present invention relates to a method for preparing optically active (R)-aryloxypropionic acid ester derivatives, and more particularly to a method for preparing (R)- aryloxypropionic acid ester derivatives with high optical purity and good yield at low cost from phenol derivatives with various substituted functional groups and (S)-alkyl O-arylsulfonyl lactates.