131860-33-8

Basic information

• Product Name: Azoxystrobin
• Synonyms: QUADRIS;pyroxystrobin;AMISTAR;Methyl (E)-2-((6-(2-cyanophenoxy)-4-pyrimidinyl)oxy)-alpha-(methoxymethylene)benzeneacetate;AZOXYSTROBIN;ICI A5504;HERITAGE;methyl (E)-2-((6-(2-cyanophenoxy)-4-pyrimidinyl)oxy)-α-(methoxymethylene)benze-neacetate
• CAS NO: 131860-33-8
• Molecular Formula: C₂₂H₁₇N₃O₅
• Molecular Weight: 403.39
• Product Categories: A-BPesticides;AntibioticsAlphabetic;A;Alpha sort;AR to AZ;Fungicides;Pesticides&Metabolites;Agro-Products;Aromatics;Heterocycles;NULL;Pharmaceutical intermediates
• Mol File: 131860-33-8.mol

Chemical Properties

• Melting Point: 118-119°
• Boiling Point: 581.3 °C at 760 mmHg
• Flash Point: 305.3 °C
• Appearance: /
• Density: 1.33
• Vapor Pressure: 1.67E-13mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: 0-6°C
• PKA: -0.93±0.18(Predicted)
• Water Solubility: 6g/L at 20℃
• CAS DataBase Reference: Azoxystrobin(CAS DataBase Reference)
• NIST Chemistry Reference: Azoxystrobin(131860-33-8)
• EPA Substance Registry System: Azoxystrobin(131860-33-8)

Safety Data

• Hazard Codes: T;N,N,T
• Statements: 23-50/53
• Safety Statements: 22-45-60-61
• RIDADR: UN 2811
• WGK Germany: 2
• Hazardous Substances Data: 131860-33-8(Hazardous Substances Data)

Usage

Chemical Description

Azoxystrobin is a fungicide used to control various fungal diseases in crops.

Uses

Used in Agriculture:
Azoxystrobin is used as a systemic, broad-spectrum fungicide for various crops, including cereals, rice, grapevines, apples, peaches, bananas, citrus, cucurbits, potatoes, tomatoes, peanuts, coffee, and turf. It is effective against fungal pathogens from all four taxonomic groups: Oomycetes, Ascomycetes, Deuteromycetes, and Basidiomycetes. The fungicide controls diseases such as rusts, downy and powdery mildew, rice blast, and apple scab.
Azoxystrobin has been processed as a Reduced Risk pesticide for Turf uses and was first introduced in 1998. It inhibits spore germination and is recognized for its effectiveness in controlling a wide range of fungal diseases. In California, the largest crop uses include almonds, rice, pistachios, wine grapes, raisins, and garlic. It is classified as a U.S. EPA Restricted Use Pesticide (RUP).

Hazard

Moderately toxic by inhalation.

Trade name

ABOUND?; AMISTAR?; AMISTAR OPTI; AMISTAR PRO; BANKIT?; HERITAGE?; ICIA5504 80WG?; OLYMPUS?; ORTIVA?; PROTEGE?; PROTEGE-ALLEGIANCE WP?;PROTEGE-FL SEED APPLIED FUNGICIDE?; QUADRIS OPTI?; QUILT?; SOYGARD WITH PROTEGE?

Safety Profile

Moderately toxic by inhalation.When heated to decomposition it emits toxic vapors ofNOx.

Potential Exposure

A β-methyoxyacrylate, Strobilurin is an agricultural fungicide.

Metabolic pathway

Azoxystrobin is a recently developed fungicide with a novel mode of action (see Overview for relevant references). It was first registered in 1996. It has been and is being subjected to the full range of studies to meet current regulatory requirements for toxicology, metabolism and environmental fate. Information on its metabolism and environmental fate was presented as a lecture at the 9th International Congress of Pesticide Chemistry (IUPAC) in 1998 and this will be published in the Proceedings. The information presented below is derived from this source (Joseph, 1998). Azoxystrobin is a carboxylic acid methyl ester and one of its pathways of metabolism is via hydrolysis to its carboxylic acid. The latter is not biologically active (see Overview) and the favourable selective toxicity of the fungicide is due to this and other metabolic reactions in non-target species. Azoxystrobin is readily degraded in soil and ultimately mineralised and it is metabolised in plants and animals. Metabolism is complex because the molecule possesses several functional groups. Five different pathways have been identified in plants and animals. Biotransformations occurring on the parent molecule include hydrolysis, aromatic hydroxylation, cleavage of both phenoxy linkages, nitrile to amide hydrolysis and fragmentation of the acrylate double bond. Some photo-induced changes also occur, including conversion to the (Z)-isomer.

Metabolism

Metabolites are also rapidly degraded in soil. Photolysis studies show a DT50 of 11 days. Due to the rapid degradation and low soil mobility, no leaching is found in field studies.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Toxicity evaluation

Azoxystrobin has an acute oral LD50 > 5,000 and an acute dermal LD50 > 2,000 mg/kg in rats. Azoxystrobin gives only slight skin and eye irritation and is nonmutagenic and nonteratogenic. Its NOEL is 18 mg/kg bw/day. It has no toxicity to birds in acute studies (LD50 > 2,000 mg/kg). It is harmless to other nontarget organisms (honey bees, earthworms, beneficial arthropods) due to low toxicity and rapid degradation in the environment, which minimizes exposure.

Degradation

Azoxystrobin is degraded under conditions of aqueous photolysis with a DT50 of 11-17 days (PM). Soil surface photolysis of azoxystrobin (14C-labelled separately in each of the three rings) was studied on a sandy loam for a period of 30 days. The fungicide was degraded with a DT50 measured as a mean of the three radiolabels, of 11 days in natural summer sunlight. The degradation was complex, affording many initial products, all at 40% of the applied radiocarbon. These products were themselves readily photolysed and no product accumulated during the course of the experiment. The yield of 14CO2 in 30 days was between 17% (phenylacrylate label) and 29% (cyanophenyl label). Thus soil surface photodegradation is likely to be an important mechanism for the removal of azoxystrobin from the environment.

Incompatibilities

Combustible; dust may form explosive with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Dispose of contents and container to an approved waste disposal plant. Use a licensed professional waste disposal service to dispose of this material. Ultimate disposal of the chemical, product, and waste containers must consider: the material’s impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with public health, local, state, and federal health and environmental regulations. Never reuse or recycle used product containers unless the recycling program specifically accepts pesticide containers and you follow the program’s instructions for preparing the empty containers for collection

InChI:InChI=1/C22H17N3O5/c1-27-13-17(22(26)28-2)16-8-4-6-10-19(16)30-21-11-20(24-14-25-21)29-18-9-5-3-7-15(18)12-23/h3-11,13-14H,1-2H3/b17-13+

Synthetic route

2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3,3-dimethoxypropionic acid methyl ester → azoxystrobin (131860-33-8)

Conditions	Yield
With dimethyl sulfate at 110℃; under 375.038 Torr; for 1.75h;

Upstream product

• 131860-97-4 (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate 
• 611-20-1 salicylonitrile 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 143230-42-6 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester 
• 1193-21-1 4,6-dichloropyrimidine 
• 143130-94-3 methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]-3-methoxyprop-2-enoate 
• 5788-17-0 methyl (2E)-3-methoxy-2-propenoate 
• 31575-75-4 2-bromophenyl benzyl ether 
• 190661-29-1 2-benzyloxyphenylboronic acid 
• 163041-47-2 (Z)-3-methoxy-2-iodo-acrylic acid methyl ester 
• 103497-78-5 (E)-3-methoxy-2-(2-benzyloxyphenyl)acrylic acid methyl ester 
• 95-56-7 2-hydroxybromobenzene 
• 187327-30-6 2-[6-(trifluoromethyl)-2-pyridyloxymethyl]phenylacetic acid methyl ester 
• 67-56-1 methanol 

Downstream Products

• 478413-45-5 2-(2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl)acetic acid methyl ester 
• 143130-94-3 methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]-3-methoxyprop-2-enoate 
• 1193-24-4 4,6-pyrimidinediol 
• 240802-59-9 2-(6-hydroxypyrimidin-4-yloxy)benzonitrile 
• 1185255-09-7 (E)-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylic acid 

Related news

Short-term developmental effects and potential mechanisms of Azoxystrobin (cas 131860-33-8) in larval and adult zebrafish (Danio rerio)08/03/2019

Previous study indicated that azoxystrobin had high acute toxicity to zebrafish, and larval zebrafish were more sensitive to azoxystrobin than adult zebrafish. The objective of the present study was to investigate short-term developmental effects and potential mechanisms of azoxystrobin in larva...detailed

Effect of Azoxystrobin (cas 131860-33-8) fungicide on the physiological and biochemical indices and ginsenoside contents of ginseng leaves08/02/2019

BackgroundThe impact of fungicide azoxystrobin, applied as foliar spray, on the physiological and biochemical indices and ginsenoside contents of ginseng was studied in ginseng (Panax ginseng Mey. cv. “Ermaya”) under natural environmental conditions. Different concentrations of 25% azoxystrobi...detailed

Reproductive toxicity of Azoxystrobin (cas 131860-33-8) to adult zebrafish (Danio rerio)08/01/2019

In the past few decades, extensive application of azoxystrobin has led to great concern regarding its adverse effects on aquatic organisms. The objective of the present study was to evaluate the reproductive toxicity of azoxystrobin to zebrafish. After adult zebrafish of both sexes were exposed ...detailed

The fungicide Azoxystrobin (cas 131860-33-8) perturbs the gut microbiota community and enriches antibiotic resistance genes in Enchytraeus crypticus07/31/2019

The use of pesticides to ensure global food security is the most important pest control strategy in modern agriculture but causes extensive soil pollution. This pollution involves potential risks to human health and ecosystems. In addition to soil animal growth, the adverse impact of pesticides ...detailed

Fungicides chlorothanolin, Azoxystrobin (cas 131860-33-8) and folpet induce transcriptional alterations in genes encoding enzymes involved in oxidative phosphorylation and metabolism in honey bees (Apis mellifera) at sublethal concentrations07/30/2019

Fungicides are highly used for plant protection but their molecular and chronic effects are poorly known. Here, we analyse transcriptional effects in the brain of honey bees of three frequently applied fungicides, azoxystrobin, chlorothanolin and folpet, after oral exposure for 24, 48 and 72 h. ...detailed

Influence of droplet size and Azoxystrobin (cas 131860-33-8) insensitivity on frogeye leaf spot management in soybean07/29/2019

Field experiments were conducted in 2014 and 2015 to evaluate the influence of droplet size on foliar fungicide efficacy and leaf residue in soybean infected with Cercospora sojina, the fungal agent of frogeye leaf spot. A fungicide premix of azoxystrobin and difenoconazole was applied using two...detailed

Parental exposure to Azoxystrobin (cas 131860-33-8) causes developmental effects and disrupts gene expression in F1 embryonic zebrafish (Danio rerio)07/28/2019

The fungicide azoxystrobin induces reproductive toxicity in adult zebrafish. However, data are lacking regarding the impact of azoxystrobin in the F1 generation after parental exposure. To address this knowledge gap, parental zebrafish (F0) were exposed to 2, 20 and 200 μg/L azoxystrobin for 21...detailed

Acute toxicity of the fungicide Azoxystrobin (cas 131860-33-8) on the diatom Phaeodactylum tricornutum07/27/2019

Azoxystrobin (AZ) is an effective broad-spectrum fungicide. Due to its extensive application, AZ is detectable in aquatic ecosystems and thus influences aquatic organisms. In this study, the acute toxicity (96 h) of AZ at concentrations of 1.0 mg/L and 5.0 mg/L on the diatom Phaeodactylum tricor...detailed

Preparation and characterization of several Azoxystrobin (cas 131860-33-8) channel solvates07/25/2019

Azoxystrobin is an important strobilurins fungicide. Nine channel solvates of azoxystrobin were obtained for the first time and six of them could be crystallized in single crystals. The crystallographic data, unit cell porosity, Hirshfeld surface, and fingerprint plot were analyzed. These solvate...detailed

Relevant articles and documents

AN IMPROVED PROCESS FOR PREPARATION OF METHYL (2E)-2-(2-{[6-(2-CYANOPHENOXY)PYRIMIDIN-4-YL]OXY}PHENYL)-3-METHOXYACRYLATE

The present invention relates to an improved processses for synthesizing preparing substituted cyanophenoxy-pyrimidinyloxy-phenyl acrylate derivatives. The present invention specifically relates to an improved process for the preparation of methyl (2E)-2-(2-{[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy}phenyl)-3-methoxyacrylate having the following Formula I.

Method for improving conversion rate of azoxystrobin

The invention discloses a method for improving the conversion rate of azoxystrobin. The method comprises the following steps: preparing methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy acrylate; preparing o-hydroxybenzonitrile; mixing methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy acrylate, o-hydroxybenzonitrile, potassium carbonate and ketene chloride according to a molar ratio of 30: 35: 50: 1.1, and dissolving the obtained mixture in dimethylformamide to obtain a mixed product; and heating the prepared mixed product, keeping the mixed product at a certain temperature, conducting filtering, carrying out reduced-pressure distillation, performing cooling, separating out crystals, carrying out filtering and washing and performing drying to obtain azoxystrobin. On the basis of the prior art, the synthesis of azoxystrobin is improved in the invention, so the yield of azoxystrobin is effectively increased, the conversion rate of the raw materials including methyl(E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy acrylate and o-hydroxybenzonitrile for azoxystrobin in the process of preparing azoxystrobin is effectively improved, and the production benefit of azoxystrobin is improved.

MENUFCACTURING METHOD OF AZOXYSTROBIN

MCMA ((E)- Methyl methyl methyl (2- ((6-chloropyrimidin-4-yl) oxy) phenyl).3 - methoxyacrylate). DABCO (1, 4-diazabicyclo [2.2.2] octane) and 2 - CP (2-cyanophenol) are mixed and fed into a reactor (z) by mixing into azoxystobin a continuous reactor and introducing them into a reactor.

PREPARATION METHOD FOR AZOXYSTROBIN AND INTERMEDIATE THEREOF

The present invention relates to the preparation field of azoxystrobin, and discloses a preparation method for a compound represented by formula (I). The method comprises the following steps: (1) a compound represented by formula (II) is hydrolyzed in a solvent under acidic conditions to obtain a compound represented by formula (III); and (2) the compound represented by formula (III) is reacted with a base and a methylating agent to obtain the compound represented by formula (I); in the formula, R3 is hydrogen or C1-C4 alkyl, and R4 is C1-C4 alkyl. The process for preparing azoxystrobin of the present invention not only successfully replaces trimethyl orthoformate and reduces the raw material cost, but also has high total reaction yield, and is suitable for industrial large-scale production. Experiments have proven that the yield of the prepared azoxystrobin can reach 95%.

METHOD FOR PREPARING AZOXYSTROBIN

A method for preparing azoxystrobin comprises the following steps: (a) mixing methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate, 2-cyanophenol, potassium carbonate, and 10-80 mol % of 1-methylpyrrolidine as a catalyst in an aprotic solvent to form a basic mixture, and reacting the basic mixture for 2-5 hrs at a temperature of 60-120° C.; and (b) subjecting the basic mixture after reaction in Step (a) to a first distillation under a reduced pressure of 80-120 torr at 70-80° C., to obtain azoxystrobin.

PROCESS FOR PREPARATION OF AZOXYSTROBIN AND INTERMEDIATES THEREOF

The present invention relates to a process for preparation of strobilurin compound, azoxystrobin and its intermediates using a catalyst selected from 1,8-Diazabicyclo[5.4.0]undec-7-ene or 1,5-Diazabicyclo[4.3.0]non-5-ene, salts thereof, or derivatives thereof.

PROCESS FOR THE PREPARATION OF FUNGICIDALLY ACTIVE STROBILURIN COMPOUNDS AND INTERMEDIATES THEREOF

The present invention relates to a process for the preparation of strobilurin of compounds of Formula (I) of and its intermediates using 1,5,7-triazabicyclo[4.4.0]dec-5-ene or salts thereof, or derivatives thereof as a catalyst. The present invention provides the compounds of formula (I) in high yield and high purity.

Method for preparing azoxystrobin

The present invention provides a process for preparing azoxystrobin, which is performed by reacting 2-cyanophenol or a salt thereof with a compound represented by formula I under the catalysis of a trimethylamine catalyst to obtain the azoxystrobin represented by formula II, which allows the yield of the product azoxystrobin to reach 98% or more, the yield of separated product to reach 95% or more and the post-processing to be simple. The trimethylamine catalyst can be recycled and reused in synthesizing the target product azoxystrobin, which not only reduces the cost but also reduces the total nitrogen and COD in wastewater. The advantages regarding of cost and environmental protection of the method according to the present invention are significant and thus the method is suitable for industrial production.

A process for preparing a azoxystrobin or intermediate catalyst and preparation method (by machine translation)

The invention relates to a process for the preparation of azoxystrobin or intermediate catalyst, containing 1 - azabicyclo [2, 2, 2] octane structure on a series of compounds introduced into the amino or substituted amino, form the formula 10 structure shown or a salt thereof; the invention also relates to processes for preparing azoxystrobin or intermediates thereof, the present invention provides catalyst and preparation method, with process is easy to control, short reaction time, the conversion is high, and low energy consumption, and is suitable for large-scale industrial production. (by machine translation)

An azoxystrobin and its intermediate synthesis method

The invention discloses a synthesis method for azoxystrobin. The synthesis method comprises the following steps of reacting a mixed system containing (E)-methyl-2-[2-(6-chloropyrimidine-4-methoxy) phenyl]-3-methoxyacrylate and methyl 2-[2-(6-chloropyrimidine-4-methoxy) phenyl]-3,3-dimethoxypropanoate with 2-hydroxy-benzonitril in the presence of a catalyst, adding metal chloride, and performing heating reaction and post-treatment to obtain azoxystrobin. The synthesis method is mild in reaction condition, and reaction can be realized under the conditions of normal pressure and negative pressure; moreover, the use of a hypertoxic catalyst such as dimethyl sulfate is avoided in a reaction process, so that safety is greatly improved, and environmental pollution is greatly reduced; the synthesis method is pure in reaction, and fewer byproducts are produced.