175013-18-0

Usage

Uses

Used in Agricultural Industry:
Pyraclostrobin is used as an agricultural fungicide for the protection of seed grass and food crops against various fungal diseases. It helps in enhancing disease resistance, increasing crop yield, and improving the overall health of the plants.
Used in Enhancing Disease Resistance:
Pyraclostrobin is used as a priming agent to induce rapid accumulation of antimicrobial PR-1 defense proteins in plants after infection with Tobacco mosaic virus and the wildfire pathogen Ps pv. tabaci. This priming effect is associated with enhanced disease resistance in various crops and ornamental plants, both in greenhouse and field conditions.
Used in Increasing Crop Yield:
Treatment with Pyraclostrobin has been shown to increase crop yield in the field. This is due to its ability to induce a 'greening effect,' which refers to the phenomenon of delayed leaf senescence and an increased grain-filling period, resulting in enhanced biomass and yield.
Used in Enhancing Resistance to Abiotic Stresses:
Pyraclostrobin-induced priming is also associated with enhanced resistance to abiotic stresses, such as drought, in the field. This further contributes to the overall health and productivity of the crops.

InChI:InChI=1/C19H18ClN3O4/c1-25-19(24)23(26-2)17-6-4-3-5-14(17)13-27-18-11-12-22(21-18)16-9-7-15(20)8-10-16/h3-12H,13H2,1-2H3

Upstream product

• 3958-60-9 2-nitrophenylmethyl bromide 
• 76205-19-1 1-(para-chlorophenyl)-3-hydroxypyrazole 
• 1334322-60-9 N-carbomethoxy-N-methoxy-(2-chloromethyl)-aniline 
• 1334322-42-7 N-hydroxy-(2-pyrrolidinomethyl)-aniline 
• 1334322-44-9 N-carbomethoxy-N-hydroxy-(2-pyrrolidinomethyl)-aniline 
• 55581-63-0 1-(2-nitro-benzyl)-pyrrolidine 
• 220368-29-6 2-[(N-4-chlorophenyl)-1H-pyrazol-3-yloxymethyl]-1-nitrobenzene 
• 76205-19-1 1-(4-chlorophenyl)-1Η-pyrazol-3-ol 
• 67-56-1 methanol 
• 74-87-3 methylene chloride 
• 74-85-1 ethene 
• 74-83-9 methyl bromide 
• 151830-35-2 methyl N-hydroxy-2-methylphenylcarbamate 
• 611-22-3 N-(o-tolyl)hydroxylamine 

Downstream Products

• 1304050-94-9 C₇H₆O₃*C₁₉H₁₈ClN₃O₄ 

Relevant academic research and scientific papers

Methyl N-methoxyphenylcarbamate preparation method

The invention discloses a methyl N-methoxyphenylcarbamate preparation method, which comprises: carrying out a stirring reaction on an N-hydroxyl group having a structure represented by a formula (1),an O-methylation reagent and a catalyst in an organic solvent under alkaline conditions, reducing the pressure, stopping the reaction, cooling, filtering, drying, removing the solvent, and re-crystallizing to obtain methyl N-methoxyphenylcarbamate having a structure represented by a formula (2), wherein the purity is 98.2%, the yield is 90.8%, R1 is halogen, and R2-R11 are H or C1-C5 alkyl.

Preparation method for high-purity pyraclostrobin

The invention relates to the technical field of compound synthesis, in particular to a preparation method for high-purity pyraclostrobin. The pyraclostrobin is synthesized from p-chloroaniline and o-nitrosotoluene as initial raw materials through the steps of diazotizing, cyclizing, oxidizing, bromizing, condensating, reducing, acylating, methylating and the like. According to the preparation method, the problem that the purity of the pyraclostrobin in the prior art is low is solved; and the preparation method for the pyraclostrobin has the advantages of high yield, high purity and high material utilization rate.

Synthesis process of pyraclostrobin

The invention discloses a synthesis process of pyraclostrobin. The synthesis process includes the process of synthesis, cyclization, oxidization, bromination, etherification, reduction, esterificationand methylation of chlorophenylhydrazine hydrochloride. According to the synthesis process of the pyraclostrobin, when 1-(4-chlorphenyl)-3-pyrazole alcohol is prepared, air oxidization is adopted, the reaction is mild, controllability is high, and the yield is improved by 5% or above compared with literature reports; in the etherification reaction, an inorganic base water solution is adopted as the acid-binding agent, an efficient phase transfer catalyst B is added, the reaction time is effectively shortened, and the reaction yield is effectively improved; a specific catalyst C is adopted, adichloroethane and ethyl alcohol mixed solution serves as the reaction solvent, the side reaction of reducing a nitryl group into an amido group is effectively controlled, the reaction yield is greatly improved to reach 95% or above.

IMPROVED PROCESS FOR THE PREPARATION OF PYRACLOSTROBIN

The present invention relates to a novel and improved process for preparation of methyl [2-({[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}methyl)phenyl]methoxycarbamate (Pyraclostrobin)of formula (I) in free form or in agrochemically acceptable salt form useful as a pest control agent starting from methyl [2-({[1-(4-chlorophenyl)-1-H-pyrazol-3-yl]oxy}methyl)phenyl]hydroxycarbamatein simple manner and in high purity and good yield.

Preparation method of high-purity pyraclostrobin

The invention provides a preparation method of high-purity pyraclostrobin. The high-purity pyraclostrobin is prepared by taking 1-(4-chlorophenyl)-3-hydroxy-1-h-pyrazole and O-nitrobenzyl bromide as raw materials and through condensation, reduction, esterification, methylation and mixed solvent separation and purification. By adopting the preparation method provided by the invention to prepare thehigh-purity pyraclostrobin, the preparation method has the characteristics that the cost is low, the product purity is high, the product yield is high, the raw materials are easy to obtain, and the like; the recycling and reusing rate of a solvent required for reaction is high, the three wastes can be preferably treated, and the purpose of clean production can be achieved.

Based on pyraclostrobin intermediate methylation synthesis method (by machine translation)

The invention discloses based on pyraclostrobin intermediate methylation synthetic method, pyraclostrobin intermediate with the phase transfer catalyst, solvent, alkaline solution and methyl chloride by reaction gas, controlling the reaction temperature and pressure, to be after the reaction, cooling, pyraclostrobin intermediate methylation product obtained. The invention synthetic method is to pyraclostrobin N - hydroxy intermediate to methylation method, the substitute methyl dimethyl sulfate, dimethyl carbonate, methyl iodide and the like as in the production process of the pyraclostrobin methylation reagent, effectively reduce the production cost and wastes, methylation yield ≥ 95.0%, HPLC external standard content ≥ 98.0%. (by machine translation)

A novel process for preparing crystalline methyl N-[2-[[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy]methyl]phenyl]-N-methoxycarbamate

The present invention relates to a process for preparing crystalline methyl N-[2-[[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy]methyl]phenyl]-N-methoxycarbamate (I), comprising a) reacting a compound of formula (II) with an alkylating agent in the presence of a base in the presence of a polar solvent selected from alcohols and ketons; b) the addition of water.

Method for simply synthesizing pyraclostrobin

The invention discloses a method for simply synthesizing pyraclostrobin. The method comprises steps as follows: N-hydroxyl-N-2-[1-(4-chlorophenyl)-3-pyrazoloxy methyl]phenyl carbamate and a phase transfer catalyst are dissolved in an organic solvent, dimethyl sulfate is added, an acid-binding agent is dropwise added at the system temperature kept in a range of 5-70 DEG C, the components react for 1-5 h, and pyraclostrobin is obtained. Under the condition of reasonable control of feeding sequence of reaction raw materials and the system temperature, the problems of many reaction by-products as well as potential safety hazard and the like due to the many reaction by-products in an existing pyraclostrobin synthesis process are effectively solved, and a plurality of advantages such as reduction of production cost, reduction of wastewater quantity in a production process and the like can be provided for industrial production, so that the method is beneficial to energy conservation, emission reduction and environment protection of pesticide chemical enterprises and is more suitable for large-scale industrial production.

Synthesis method of pyraclostrobin

The invention relates to a synthesis method of pyraclostrobin. The method comprises the following steps: 1) adding N-hydroxy-N-2-[N-(4-chlorophenyl) pyrazolyl-3-oxymethyl]aniline and triethylamine into a reaction solution, stirring, and heating; 2) dropwisely adding iodomethane to carry out methylation reaction, and keeping the temperature; 3) neutralizing by washing with water, and standing to stratify; and 4) recovering methylbenzene, adding isopropanol, crystallizing, and filtering to obtain the pyraclostrobin pure product. The synthesis method reduces the damage to the human body and environment, and requires low acid-binding agent consumption. The method enhances the yield of the product, and further lowers the generation of byproducts. The method is simple to operate, and has the advantages of high raw material conversion rate and high yield and content (respectively 98% or above).

Method for catalytically synthesizing pyraclostrobin

The invention discloses a method for catalytically synthesizing pyraclostrobin, relating to the technical fields of chemical industry and pesticide intermediate preparation. The method comprises the following steps: adding a compound II N-hydroxy-N-2-[(N-p-chlorphenyl)-3-pyrazolyloxymethyl]carbanilate into a two-phase solvent, adding a phase-transfer catalyst, and meanwhile, dropwisely adding an acid-binding agent water solution and dimethyl sulfate to carry out etherification reaction on the compound II N-hydroxy-N-2-[(N-p-chlorphenyl)-3-pyrazolyloxymethyl]carbanilate and dimethyl sulfate while keeping the pH value of the reaction system at 8-9, thereby obtaining the compound I pyraclostrobin. The method has the advantages of short reaction time and high product yield, lowers the production cost, and reduces the generated wastewater, thereby being beneficial to environment protection.