6597-79-1

Basic information

• Product Name: Acetyl chloride, (4-chloro-2-methylphenoxy)-
• CAS NO: 6597-79-1
• Molecular Formula: C9H8Cl2O2
• Molecular Weight: 219.067
• Mol File: 6597-79-1.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: Acetyl chloride, (4-chloro-2-methylphenoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetyl chloride, (4-chloro-2-methylphenoxy)-(6597-79-1)
• EPA Substance Registry System: Acetyl chloride, (4-chloro-2-methylphenoxy)-(6597-79-1)

Safety Data

• Hazardous Substances Data: 6597-79-1(Hazardous Substances Data)

Upstream product

• 94-74-6 MCPA 
• 2436-73-9 methyl 2-(4-chloro-2-methylphenoxy)acetate 
• 1570-64-5 2-methyl-4-chlorophenol 

Downstream Products

• 64046-49-7 (4-chloro-2-methylphenoxy)-2-acetoxyethyldimethylammonium hydrochloride 
• 100713-87-9 2-[(4-chloro-2-methyl-phenoxy)-acetoxy]-propionic acid methyl ester 
• 29923-08-8 N-[(4-chloro-2-methyl-phenoxy)-acetyl]-DL-aspartic acid 
• 6294-35-5 (4-chloro-2-methyl-phenoxy)-acetic acid-[2-((1R)-6,6-dimethyl-norpin-2-en-2-yl)-ethyl ester] 
• 22716-96-7 (4-chloro-2-methyl-phenoxy)-thioacetic acid 
• 403-97-4 (4-chloro-2-methyl-phenoxy)-acetic acid-(3-trifluoromethyl-anilide) 
• 53442-82-3 C₁₄H₁₈ClNO₃ 
• 53442-81-2 C₁₃H₁₆ClNO₃ 
• 20951-51-3 (4-Chloro-2-methyl-phenoxy)-acetic acid 4-methanesulfonyl-phenyl ester 
• 20951-36-4 (4-Chloro-2-methyl-phenoxy)-acetic acid 2,6-dibromo-4-methanesulfonyl-phenyl ester 
• 19443-50-6 2-(4-Chloro-2-methyl-phenoxy)-N-(octahydro-naphthalen-4a-yl)-acetamide 
• 26675-36-5 (4-Chloro-2-methyl-phenoxy)-acetic acid 2,6-dibromo-4-[(2,4-dinitro-phenoxyimino)-methyl]-phenyl ester 
• 97442-49-4 4-Chlor-2-methyl-phenoxyessigsaeure-(2-diethylaminoethylamid) 
• 128998-07-2 (4-Chloro-2-methyl-phenoxy)-acetic acid 6-hydroxymethyl-4-oxo-4H-pyran-3-yl ester 

Relevant articles and documents

Novel esterquat-based herbicidal ionic liquids incorporating MCPA and MCPP for simultaneous stimulation of maize growth and fighting cornflower

Modern agricultural practices are often based on the use of mixtures of specific herbicides to achieve efficient crop protection. The major drawbacks of commercial herbicidal formulations include the necessity to incorporate toxic surfactants and high volatility of active substances. Transformation of herbicides into herbicidal ionic liquids (HILs) seems to be a promising alternative which allows to almost completely reduce volatility due to ionic interactions. In the scope of this research, we transformed (2-methyl-4-chlorophenoxy)acetic acid (MCPA) into a quaternary ester (esterquat) with the use of derivatives of 2-dimethylaminoethanol. The obtained esterquats were later coupled with (±)?2-(4-chloro-2-methylphenoxy)propionic acid (MCPP) in the form of an anion. The combination of MCPA and MCPA is commonly applied in the UK, EU countries and also in the USA to increase the spectrum of targeted weed species. In the framework of this study, novel HILs with an esterquat moiety incorporating a long alkyl chain (C8, C9, C10, C11, C12, C14) were prepared and characterized in terms of basic physicochemical properties (solubility and volatility) as well as biodegradability. Their phytotoxicity was assessed towards cornflower (Centaurea cyanus) as a model weed and maize (Zea mays) as a crop plant. The presence of the esterquat cation contributed to satisfactory solubility in water and other low polar solvents, which eliminates the need to add exogenous adjuvants. Further experiments indicated that the tested HILs stimulated the germination stage of maize and maintained high herbicidal activity towards cornflower. No significant differences in terms of properties were observed in case of HILs which included alkyl substituents with an odd number of carbon atoms. Future studies should be focused on structural modifications in order to improve the biodegradability as well as field studies for evaluation of commercial applications.

Design and Synthesis of Novel 4-Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action

In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha-1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha-1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.

Synthesis and Biological Activity of 4-[(Substituted Phenoxyacetoxy)methyl]-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-1-one

A series of novel 4-[(substituted phenoxyacetoxy)methyl]-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-1-one 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o were synthesized. Their structures were confirmed by IR,1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 4b, 4c, 4f, 4h, 4i, and 4j possess 90–100% inhibition against the growth of roots of both rape and barnyard grass at 10 mg/L. Moreover, the title compounds 4f, 4g, and 4h possess 75–89% inhibition against Botrytis cinerea at the concentration of 50 mg/L.