6597-79-1

Upstream product

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

Downstream Products

• 64046-49-7 (4-chloro-2-methylphenoxy)-2-acetoxyethyldimethylammonium hydrochloride 
• 102374-57-2 (4-chloro-2-methyl-phenoxy)-acetic acid-(1-phenyl-2-pyrrolidino-ethyl ester); hydrochloride 
• 53442-82-3 C₁₄H₁₈ClNO₃ 
• 53442-81-2 C₁₃H₁₆ClNO₃ 
• 53442-87-8 C₁₆H₂₂ClNO₃ 
• 53442-89-0 C₁₆H₂₂ClNO₃ 
• 53442-84-5 C₁₆H₂₂ClNO₃ 
• 53442-86-7 C₁₇H₂₄ClNO₃ 
• 53442-83-4 C₁₈H₂₆ClNO₃ 
• 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) 

Relevant academic research and scientific papers

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.

Cyhalofop-containing pesticide composition and application thereof

The invention discloses a pesticide composition containing cyhalofop-butyl and application thereof, belongs to the technical field of pesticide preparation and comprises 10 - 20 parts of cyhalofop-butyl. Tetramethyl chloride 3-5 parts, synergistic microcapsule 8-13 parts, wetting agent 1.5 - 4.5 parts, dispersing agent 1-3 parts, defoaming agent 0.5 - 1.5 parts and water 40 - 50 parts. When the water in the soil is less, the weed is absorbed by the chitosan so as to accelerate the absorption of A the synergic microcapsule and the cyhalofop-butyl ester, so that the pesticide composition is greatly reduced per mu.

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.

Esterquat herbicidal ionic liquids (HILs) with two different herbicides: Evaluation of activity and phytotoxicity

Herbicidal ionic liquids (HILs) constitute a new concept in crop protection products. Their main advantage is the potential to combine the efficiency of traditional herbicides with low vapour pressure and adjustable water solubility which leads to improved environmental safety in the agricultural sector. Among many strategies to obtain new HILs, esterquats seem to be well suited for modification since both the cation and anion may be constituents of herbicides. In the framework of this study 16 new esterquat HILs were synthetized based on standard herbicides: 2,4-D, MCPA, MCPP, 4-CPA, Clopyralid and Dicamba. Germination tests performed on agricultural soil using cornflower indicated the best two HILs. Furthermore, analysis of the toxicological effects of HILs on wheat plants revealed an additional advantage of the two selected HILs. The glutathione (GSH) content and glutathione S-transferase (GST) activity showed a lower oxidative stress level in wheat plants treated with examined HILs, respectively, in comparison to a mixture of reference compounds. Finally the Ames test was applied in order to analyse the mutagenic activity of the two selected HILs.

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.

Synthesis and Biological Activity of Ethyl 4-Alkyl-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylate

(Chemical Equation Presented) A series of novel ethyl 4-(methyl or trifluoromethyl)-2-(2-(substituted phenoxy)acetamido)thiazole-5-carboxylates 7a, 7b, 7c, 7d, 7e and 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were synthesized, and their structures were confirmed by IR, 1H-NMR, MS spectra and elemental analysis. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal activities. Compared with the fluorine free compounds 7a, 7b, and 7e, the compounds bearing fluorine 8g, 8j, and 8q showed higher herbicidal activities with 70-100% inhibition against Capsella bursa-pastoris, Amaranthus restroflexus, and Eclipta prostrata at the dosage of 150 g/ha, which indicated that the trifluoromethyl on the thiazole ring was beneficial for the herbicidal activity. Furthermore, compounds 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r were tested for fungicidal activity against Pseudoperonospora cubensis at 500 μg/mL. Compounds 8f and 8q showed the best fungicidal activity with more than 80% inhibition.

Substituted phenoxyacetate compound as well as preparation method and applications thereof

The invention provides a substituted phenoxyacetate compound as well as a preparation method and applications thereof. The substituted phenoxyacetate compound disclosed by the invention is prepared by taking substituted phenoxyacetate (2,4-D, agroxone) as a raw material through the steps of acylation and nucleophilic substitution, and the structural formula of the substituted phenoxyacetate compound is shown in a formula I. The prepared compound is novel in structure, and has the advantages of high activity, quick acting, strong selectivity, and the like. The compound is simple in preparation process, environmentally friendly, and short in reaction process. The compound has good biological activity to broadleaf weeds (e.g., kochia scoparia, quinoa), and the biological activity of part of the compound is obviously higher than that of the parent compound.

Substituted phenoxyacetic acid weeding oligomer as well as preparation method and application thereof

The invention provides a substituted phenoxyacetic acid weeding oligomer as well as a preparation method and an application thereof. Substituted phenoxyacetic acid (2,4-D, agroxone) and a nucleophilic bridging body are taken as raw materials, and acylation, nucleophilic substitution reaction are carried out, so that the substituted phenoxyacetic acid weeding oligomer is obtained, and a structural formula of the substituted phenoxyacetic acid weeding oligomer is shown in a formula I. The prepared compound has good biological activity on broadleaf weeds (such as kochia scoparia and chenopodium album), and biological activity of some compounds is obviously higher than that of a parent compound. The substituted phenoxyacetic acid weeding oligomer has the advantages of simple preparation technology, environmental friendliness and short reaction mechanism.

Synthesis and biological activity of 1-(Substituted phenoxyacetoxy)- 1-(pyridin-2-yl or thien-2-yl)methylphosphonates

A series of novel O,O-dimethyl 1-(substituted phenoxyacetoxy)-1-(pyridin-2-yl or thien-2-yl)methylphosphonates 6a-n and 7a-d 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 6a, 6c, 6l, 6m, and 7d possess 90-100% inhibition against most of the tested plants at the dosage of 1500 g ai/ha, whereas the title compounds 6b, 6g-h and 6n possess 92-100% inhibition against Fusarium oxysporum, Phyricularia grisea, Botrytis cinereapers, Gibberella zeae, Sclerotinia sclerotiorum, and Cercospora beticola at the concentration of 50mg/L.

Synthesis and evaluation of anticonvulsant activity of some N-[(4-Chlor-2-methylphenoxy)ethyl]- and N-[(4-Chlor-2-methylphenoxy)acetyl] aminoalkanols

A new series of N-(4-chlor-2-methylphenoxy)ethyl- (1-6) and N-(4-chlor-2-methylphenoxy)acetylaminoalkanols (7-10) has been synthesized for evaluation of their anticonvulsant activity. Pharmacological tests included maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole seizure (ScMet) assays, as well as rotarod for neurotoxicity (TOX) and were performed in mice i.p. and rats p.o. The activity of the compounds in the group was various, and the most active compound in mice was R,S-1N-[(4-chlor-2-methylphenoxy) ethyl]aminopropan-2-ol, revealing 100% activity in MES test at 30 mg/kg b.w., 0.5 h after administration without toxicity at the same dose and time. In rats (p.o.), the most active compound was 2N-[(4-chlor-2-methylphenoxy)ethyl]amino-2- methylpropan-1-ol, revealing 25% activity in MES at 30 mg/kg b.w. 0.5 and 1 h after administration.