99210-92-1

Upstream product

• 67-56-1 methanol 
• 3307-39-9 2-(4-chlorophenoxy)propionic acid 
• 20047-41-0 methyl (2S)-2-bromopropanoate 
• 1121-74-0 potassium 4-chlorophenoxide 
• 186581-53-3 diazomethane 
• 3307-39-9 (R)-2-(4-chlorophenoxy)propanoic acid 
• 27871-49-4 (S)-Methyl lactate 
• 106-48-9 4-chloro-phenol 
• 73246-45-4 methyl-(S)-2-chloropropionate 
• 17392-83-5 (R)-Methyl lactate 
• 95262-84-3 2-(4-chlorophenoxy)propanoic acid methyl ester 

Downstream Products

• 82703-23-9 (R)-2-(4-chlorophenoxy)-propoxyamine 
• 92471-63-1 (R)-2-methyl-2-(4-chlorophenoxy)ethanol 
• 545375-97-1 (-)-(R)-4-methyl-1-[2-(4-chlorophenoxy)-1-oxopropyl]piperidine 
• 314263-24-6 (R)-2-(4-Chloro-phenoxy)-propionyl chloride 
• 3307-39-9 (R)-2-(4-chlorophenoxy)propanoic acid 

Relevant academic research and scientific papers

Pesticide composition, application thereof and herbicide

The invention relates to the field of pesticides, and discloses a pesticide composition, applications thereof, and a herbicide, the composition contains a weeding effective amount of a component A and a component B, the content weight ratio of the component A to the component B is 1: (0.5-70), the component A is a compound 168 represented by a formula (I), and the component B is cyhalofop butyl represented by a formula (II); optionally, the composition also contains a component C as shown in a formula (III) which is described in the specification. The pesticide composition and the herbicide provided by the invention can overcome the defect that gramineous weeds such as barnyard grass, moleplant seeds, digitaria sanguinalis and leersia oryzae in a paddy field have resistance to aryloxyphenoxypropionate herbicides such as cyhalofop-butyl, can overcome the defect that phytotoxicity is easily generated to crops such as rice when cyclohexenone herbicides are used for preventing and controlling weeds, have an excellent weeding effect and have very good safety to the crops such as the rice.

Identification of anthranilic acid derivatives as a novel class of allosteric inhibitors of hepatitis C NS5B polymerase

A series of potent anthranilic acid-based inhibitors of the hepatitis C NS5B polymerase has been identified. The inhibitors bind to a site on NS5B between the thumb and palm regions adjacent to the active site as determined by X-ray crystallography of the enzyme-inhibitor complex. Guided by both molecular modeling and traditional SAR, the enzyme activity of the initial hit was improved by approximately 100-fold, yielding a series of potent and selective NS5B inhibitors with IC50 values as low as 10 nM. These compounds were also inhibitors of the HCV replicon in cultured HUH7 cells.

Microbial deracemization of α-substituted carboxylic acids: Control of the reaction path

A novel approach to preparing optically active α-substituted carboxylic acids using the whole cells of Nocardia diaphanozonaria JCM 3208 is described. When 2-phenylthiopropanoic acid and 2-methyl-3-phenylpropanoic acid were subjected to the reaction under aerobic conditions, the oxidation reaction proceeded preferentially rather than deracemization of these substrates. Herein, we report the design of reaction conditions to increase the deracemization activity in preference to oxidation reactions. In addition, we have successfully detected a metabolic intermediate in the reaction mixture of 2-methyl-3-phenylpropanoic acid, which indicates that the deracemization is a competitive reaction against the α-oxidation pathway of fatty acid metabolism.

Synthesis of chiral 1-[ω(4-chlorophenoxy)alkyl]-4-methylpiperidines and their biological evaluation at σ1, σ2, and sterol δ8-δ7 isomerase sites

Sumitomo's patented σ ligand 1-[3-(4-chlorophenoxy)propyl]-4-methylpiperidine (15), which has been claimed as agent for CNS disorders and neuropathies, and its lower homologue 12 were prepared along with related chiral (4-chlorophenoxy)alkylpiperidines. They were tested at σ1, σ2, and sterol Δ8-Δ7 isomerase (SI) sites by in vitro radioligand binding assays, to evaluate the influence of a chiral center in the alkyl chain on the selective σ1 binding relative to other σ family sites. Generally high σ1-site affinities were found, so that the chirality introduced by a methyl substitution resulted in slight differences. Nevertheless, the shorter oxyethylenic chain was beneficial to increase σ1 selectivity. However, the (-)-(S)-4-methyl-1-[2-(4-chlorophenoxy)1-methylethyl]piperidine ((-)-(S)-17) reached the highest σ1 affinity (Ki = 0.34 nM) and the best selectivity relative to the σ2 site (547-fold). Compound (-)-(S)-17 displayed also a moderate selectivity (11-fold) relative to the SI site.

Enantioselective hydrolysis of some 2-aryloxyalkanoic acid methyl esters and isosteric analogues using a penicillin G acylase-based HPLC monolithic silica column

A technique based on liquid chromatography has been developed to facilitate studies of enantioselectivity in penicillin G acylase (PGA)-catalyzed hydrolysis of some 2-aryloxyalkanoic acid methyl esters and isosteric analogues. PGA was covalently immobilized on an aminopropyl monolithic silica support to create an immobilized HPLC-enzyme reactor. Two sets of experimental data were drawn to calculate the enantioselectivity (E) of the kinetically controlled enantiomer-differentiating reaction, the degree of substrate conversion and the enantiomeric excess of the product. The developed enzymatic reactor was coupled through a switching valve to an achiral analytical column for separation and quantitation of the hydrolysis products. The enantiomeric excess was determined off-line on a PGA-chiral stationary phase. In this way, highly precise E values were determined. A computational study related to the hydrolysis of the considered racemic esters was also carried out in order to unambiguously clarify both the substrate specificity and the enantioselectivity displayed by PGA.

Microbial deracemization of α-substituted carboxylic acids: Substrate specificity and mechanistic investigation

A new enzymatic method for the preparation of optically active α-substituted carboxylic acids is reported. This technique is called deracemization reaction, which provides us with a route to obtain the enantiomerically pure compounds, theoretically in 100% yield starting from the racemic mixture. This means that the synthesis of a racemate is almost equal to the synthesis of the optically active compound, and this concept is entirely different from the commonly accepted one in the asymmetric synthesis. Using the growing cell system of Nocardia diaphanozonaria JCM3208, racemates of 2-aryl- and 2-aryloxypropanoic acid are deracemized smoothly and (R)-form-enriched products are recovered in high chemical yield (>50%). In addition, using optically active starting compounds and deuterated derivatives as well as inhibitors, we have disclosed the fact that a new type of enzyme takes part in this biotransformation, and that the reaction proceeds probably via the same mechanism as that in rat liver.

Microbial deracemization of alpha-substituted carboxylic acids.

An enzyme system of Nocardia diaphanozonaria JCM 3208 catalyzes the inversion of the chirality of various alpha-substituted carboxylic acids, such as 2-phenylpropanoic acid and 2-phenoxypropanoic acid derivatives, via a novel deracemization reaction.

Candida cylindracea lipase-mediated kinetic resolution of α-substituted α-aryloxyacetic acid methyl esters

Hydrolysis of several α-alkyl-α-aryloxyacetic acid methyl esters and of α-methyl-α-(n-propyl)-α-(p-chlorophenoxy)acetic acid methyl ester were performed in the presence of Candida cylindracea lipase. The α-alkyl-α-aryloxyacetic acid methyl esters and α-methyl-α-(n-propyl)-α-(p-chlorophenoxy)acetic acid methyl ester were incubated in buffer phosphate (pH 7-8). The reaction mixture, containing the unreacted ester and corresponding acid, showed enantiomeric excesses (ee) up to 81%. The extent of conversion was quite low for the α-methyl-α-(n-propyl)-α-(p-chlorophenoxy)acetic acid methyl ester, the corresponding acid was obtained with ee > 98%.

Optical resolution of aryloxypropionic acids and their esters by HPLC on cellulose tris-3,5-dimethyl-triphenylcarbamate derivative

Chiral chromatographic resolution of a series of antiphlogistic 2- aryloxypropionic acids and their methyl and ethyl esters was performed using a Chiralcel OD column. The CSP selected resolved most of the acids and esters efficiently, the enantiomers being well separated without requiring time consuming analysis. Chromatographic separation of R enriched samples was performed to determine the correct elution order. Using eluting systems such as hexane and 2-propanol, or hexane, 2-propanol and formic acid, the S enantiomer of all acids and esters was always found to elute first. We also considered the role of electron-donating or electron-withdrawing substituents (at the aryloxylic moiety) on the chiral resolution. It was shown that the electronic features of the substituents have more influence on the chiral interactions between the solutes and the CSP than their steric hindrance. Finally we determined, by molecular models, the interaction between CSP and solutes. In this way were able to determine all the potential sites for interactions, which are compatible with the conformations of the compounds and the structure of the stationary phase, and point out those interactions which enable chiral resolution.