76578-14-8

Basic information

• Product Name: Quizalofop-ethyl
• Synonyms: All-in-one;Assure (Du Pont);Assure Ⅱ (Du Pont);Pilot (Schering AG);pilot Super (Schering AG);Targa.Targa Dt(Rh one-Poulenc),Targa Super;QUIZALOFOP ETHYL, 100MG, NEAT;QUIZALOFOP-ETHYL PESTANAL, 50 MG
• CAS NO: 76578-14-8
• Molecular Formula: C₁₉H₁₇ClN₂O₄
• Molecular Weight: 372.8
• Mol File: 76578-14-8.mol

Chemical Properties

• Melting Point: 92-93°
• Boiling Point: bp0.2 220°
• Flash Point: 100 °C
• Appearance: /
• Density: 1.2671 (rough estimate)
• Vapor Pressure: 3.05E-10mmHg at 25°C
• Refractive Index: 1.6800 (estimate)
• Storage Temp.: 0-6°C
• PKA: -1.39±0.48(Predicted)
• Water Solubility: 303ug/L(temperature not stated)
• Merck: 13,8178
• BRN: 7145610
• CAS DataBase Reference: Quizalofop-ethyl(CAS DataBase Reference)
• NIST Chemistry Reference: Quizalofop-ethyl(76578-14-8)
• EPA Substance Registry System: Quizalofop-ethyl(76578-14-8)

Safety Data

• Hazard Codes: Xn
• Statements: 21/22
• Safety Statements: 22-24/25
• RIDADR: UN3077 9/PG 3
• WGK Germany: 3
• RTECS: UA2458255
• Hazardous Substances Data: 76578-14-8(Hazardous Substances Data)

Usage

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A halogenated ester and amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Trade name

ASSURE?[C]; DPX-Y 6202?; FBC?; 32197; INY-6202; MATADOR?; LEOPARD EC (p-isomer); MON? 78746; NC-302?; PILOT?; SUPER MATADOR (p-isomer); TARGA?; ULTRA TARGA (p-isomer)

Potential Exposure

A chlorophenoxy/aryloxyphenoxypro- pionate herbicide

Environmental Fate

Plant. Rapidly hydrolyzed in plants to quizalofop and ethanol (Humburg et al., 1989).

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous haz- ardous material, Technical Name Required.

Waste Disposal

It is the responsibility of chem- ical waste generators to determine the toxicity and physical properties and of a discarded chemical and to properly iden- tify its classification and certification as a hazardous waste and to determine the disposal method. United States Environmental Protection Agency guidelines for the classifi- cation determination are listed in 40 CFR Parts 261.3. In addi- tion, waste generators must consult and follow all regional, national, state, and local hazardous waste laws to ensure com- plete and accurate classification and disposal methods.

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

Upstream product

• 74497-15-7 (L) Ethyl 2-chloropropanoate 
• 76578-79-5 6-chloro-2-(4-hydroxyphenoxy)quinoxaline 
• 687-47-8 (S)-Ethyl lactate 
• 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 

Downstream Products

• 200509-41-7 (RS)-tetrahydrofuran-2-ylmethyl (R)-2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propionate 
• 94051-08-8 quizalofop-p 

Relevant articles and documents

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)

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.

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.

Method for producing high melting point crystals of phenoxypropionic acid derivative

A method for producing β crystals of ethyl (R)-2-[4-(6-chloro-2-quinoxalin-2-yloxy)phenoxy]propionate, which is characterized by heating α crystals, or α a crystals and β crystals, within a range of from 50° C. to lower than the melting point of the α crystals.