117428-22-5

Basic information

• Product Name: Picoxystrobin
• Synonyms: PICOXYSTROBIN;ZA1963;METHYL (E)-ALPHA-METHOXYMETHYLENE-2-(3-TRIFLUOROMETHYL-2-PYRIDYLOXYMETHYL)PHENYLACETATE;ACANTO;Benzeneacetic acid, .alpha.-(methoxymethylene)-2-6-(trifluoromethyl)-2-pyridinyloxymethyl-, methyl ester, (.alpha.E)-;methyl (e)-α-methoxymethylene-2-(3-trifluoromethyl-2-pyridyloxymethyl)phenylacetate;Methyl (E)-3-methoxy-2-{2-[6-(trifluoromethyl)-2-pyridyloxymethyl]phenyl}acrylate;Picoxystrobin [iso]
• CAS NO: 117428-22-5
• Molecular Formula: C₁₈H₁₆F₃NO₄
• Molecular Weight: 367.32
• EINECS: 1806241-263-5
• Product Categories: Pesticide
• Mol File: 117428-22-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 75°
• Boiling Point: 453.1 °C at 760 mmHg
• Flash Point: 227.9 °C
• Appearance: /
• Density: d20 1.4
• Vapor Pressure: 2.12E-08mmHg at 25°C
• Refractive Index: 1.521
• PKA: -1.09±0.24(Predicted)
• Water Solubility: 3.25mg/L at 20℃
• CAS DataBase Reference: Picoxystrobin(CAS DataBase Reference)
• NIST Chemistry Reference: Picoxystrobin(117428-22-5)
• EPA Substance Registry System: Picoxystrobin(117428-22-5)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN 3077
• WGK Germany: 2
• Hazardous Substances Data: 117428-22-5(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 117428-22-5 differently. You can refer to the following data:
1. Picoxystrobin, as a kind of Strobilurin analogues, is a kind of fungicide. It can be used for control of many kinds of fungal diseases such as yellow, brown, crown rusts, powdery mildew, and sooty mold, net and leaf blotch as well as tan spot occurring on cereal crops such as wheat, barley and oats and rye. It takes effect through inhibiting the electron transfer in mitochondria, further inhibiting the fungal respiration, disrupting metabolism and stopping the growth of the related fungi. It has both preventative and curative properties. It can be used either as a single fungicide or in combination with other fungicides such as Cyproconazole and cyprodinil.
2. Picoxystrobin (methyl (E)-3-methoxy-2-[22(6-trifluoromethyl- 2-pyridyloxymethyl)phenyl]acrylate from Zeneca Agrochemicals (now Syngenta Crop Protection) was first described by Godwin et al. (33), and is being developed for broad-spectrum control of cereal diseases. The redistribution properties of the molecule, which combine xylem systemicity and vapor phase activity, are considered important in achieving high levels of control of a range of diseases. Picoxystrobin has favorable safety and environmental profiles, and enhances grain yield and quality.

References

https://www.scbt.com/scbt/product/potassium-periodate-7790-21-8 https://en.wikipedia.org/wiki/Potassium_periodate

Uses

Different sources of media describe the Uses of 117428-22-5 differently. You can refer to the following data:
1. Picoxystrobin is an methoxyacrylate strobilurin fungicide designed for the control of wide range of cereal diseases.
2. Agricultural fungicide.

Definition

ChEBI: An enoate ester that is the methyl ester of (2E)-3-methoxy-2-[2-({[6-(trifluoromethyl)pyridin-2-yl]oxy}methyl)phenyl]prop-2-enoic acid. A cereal fungicide used to control a wide range of diseases including brown rust, tan spot, powdery mi dew and net blotch.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C18H16F3NO4/c1-24-11-14(17(23)25-2)13-7-4-3-6-12(13)10-26-16-9-5-8-15(22-16)18(19,20)21/h3-9,11H,10H2,1-2H3/b14-11+

Synthetic route

2-hydroxy-6-trifluoromethylpyridine (34486-06-1) + methyl (E)-2-(2-bromomethylphenyl)-3-methoxyacrylate (117428-49-6) → picoxystrobin (117428-22-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; Inert atmosphere;	98%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;	98%

methyl (E)-3-methoxy-2-(2-chloromethylphenyl)acrylate (117428-51-0) + 2-hydroxy-6-trifluoromethylpyridine potassium (387398-47-2) → picoxystrobin (117428-22-5)

Conditions	Yield
In N,N-dimethyl acetamide at 90℃; for 5h; Solvent; Temperature;	88.5%

methyl (E)-3-methoxy-2-(2-chloromethylphenyl)acrylate (117428-51-0) + 2-hydroxy-6-trifluoromethylpyridine sodium → picoxystrobin (117428-22-5)

Conditions	Yield
In N,N-dimethyl-formamide at 115℃; for 3h; Solvent; Temperature;	88.4%

2-[6-(trifluoromethyl)-2-pyridyloxymethyl]phenylacetic acid methyl ester (187327-30-6) + trimethyl orthoformate (149-73-5) → picoxystrobin (117428-22-5)

Conditions	Yield
With acetic anhydride at 60 - 100℃; for 18.5h; Temperature;	87.2%

2-[6-(trifluoromethyl)-2-pyridyloxymethyl]phenylacetic acid methyl ester (187327-30-6) + dimethyl sulfate (77-78-1) + trimethyl orthoformate (149-73-5) → picoxystrobin (117428-22-5)

Conditions	Yield
Stage #1: trimethyl orthoformate With titanium tetrachloride In 1,2-dichloro-ethane at 10 - 20℃; for 1h; Inert atmosphere; Stage #2: 2-[6-(trifluoromethyl)-2-pyridyloxymethyl]phenylacetic acid methyl ester In 1,2-dichloro-ethane at 0 - 20℃; for 2h; Inert atmosphere; Stage #3: dimethyl sulfate Reagent/catalyst; Temperature; Further stages;	85.1%

C17H14F3NO4 + dimethyl sulfate (77-78-1) → picoxystrobin (117428-22-5)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In toluene at 20 - 50℃; for 5h;	81.5%

(E)-methyl 2-[2-(6-trifluoromethylpyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylate (187327-31-7) + dimethyl sulfate (77-78-1) → picoxystrobin (117428-22-5)

Conditions	Yield
With potassium carbonate In hexane; N,N-dimethyl-formamide
With potassium carbonate In N,N-dimethyl-formamide at 20 - 26℃; for 6h;

2-[6-(trifluoromethyl)-2-pyridyloxymethyl]phenylacetic acid methyl ester (187327-30-6) → picoxystrobin (117428-22-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene / 90 - 120 °C 2: water; hydrogenchloride / 3 h / 20 °C 3: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / toluene / 5 h / 20 - 50 °C View Scheme

methyl 2-(chloromethyl)phenylacetate (95360-33-1) → picoxystrobin (117428-22-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; 15-crown-5 / toluene / 2 h / Reflux 1.2: 2 h / 75 °C 2.1: sodium methylate / toluene / 6 h / 20 - 26 °C / Inert atmosphere 3.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 20 - 26 °C View Scheme

isochroman-3-one (4385-35-7) → picoxystrobin (117428-22-5)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride / 2.5 h / 20 - 26 °C 2.1: sodium hydroxide; 15-crown-5 / toluene / 2 h / Reflux 2.2: 2 h / 75 °C 3.1: sodium methylate / toluene / 6 h / 20 - 26 °C / Inert atmosphere 4.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 20 - 26 °C View Scheme

(E)-methyl 3-methoxy-2-(2-methylphenyl)propenoate (103455-45-4) → picoxystrobin (117428-22-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 80 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 3 h / 80 °C 2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 50 °C View Scheme

methyl (E)-3-methoxy-2-(2-chloromethylphenyl)acrylate (117428-51-0) + 2-hydroxy-6-trifluoromethylpyridine (34486-06-1) → picoxystrobin (117428-22-5)

Conditions	Yield
With potassium carbonate In acetone for 7h; Reflux;	38.2 g

2-chloro-6-trifluoromethylpyridine (39890-95-4) → picoxystrobin (117428-22-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 3 h / 140 °C / 2625.26 Torr / Autoclave 2: N,N-dimethyl-formamide / 3 h / 115 °C View Scheme
Multi-step reaction with 2 steps 1: potassium hydroxide / water / 3 h / 180 °C / 9000.9 Torr / Autoclave 2: N,N-dimethyl acetamide / 5 h / 90 °C View Scheme

2-fluoro-6-(trifluoromethyl)pyridine → picoxystrobin (117428-22-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; tetrabutylammomium bromide / water / 10 h / 160 °C / 9000.9 Torr / Autoclave 2: N,N-dimethyl-formamide / 3 h / 115 °C View Scheme
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium hydroxide / water / 10 h / 90 °C 2: N,N-dimethyl acetamide / 5 h / 90 °C View Scheme

C18H18F3NO4 → picoxystrobin (117428-22-5)

Conditions	Yield
With dimethyl sulfate; sodium hydroxide In dichloromethane

Upstream product

• 187327-31-7 (E)-methyl 2-[2-(6-trifluoromethylpyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylate 
• 77-78-1 dimethyl sulfate 
• 117428-51-0 methyl (E)-3-methoxy-2-(2-chloromethylphenyl)acrylate 
• 34486-06-1 2-hydroxy-6-trifluoromethylpyridine 
• 387398-47-2 2-hydroxy-6-trifluoromethylpyridine potassium 
• 39890-95-4 2-chloro-6-trifluoromethylpyridine 
• 94239-04-0 2-fluoro-6-(trifluoromethyl)pyridine 
• 187327-30-6 2-[6-(trifluoromethyl)-2-pyridyloxymethyl]phenylacetic acid methyl ester 
• 149-73-5 trimethyl orthoformate 
• 117428-49-6 methyl (E)-2-(2-bromomethylphenyl)-3-methoxyacrylate 
• 103455-45-4 (E)-methyl 3-methoxy-2-(2-methylphenyl)propenoate 
• 4385-35-7 isochroman-3-one 
• 95360-33-1 methyl 2-(chloromethyl)phenylacetate 

Related news

Hapten synthesis, monoclonal antibody generation, and development of competitive immunoassays for the analysis of Picoxystrobin (cas 117428-22-5) in beer07/20/2019

This paper describes the original synthesis of a functionalized derivative of the fungicide picoxystrobin and the generation of the first reported monoclonal antibodies against this strobilurin pesticide. The synthetic hapten was prepared by total synthesis from commercial chemicals and incorpor...detailed

Development of monoclonal antibody-based competitive immunoassays for the detection of Picoxystrobin (cas 117428-22-5) in cereal and oilseed flours07/21/2019

Picoxystrobin is a new generation fungicide primarily developed to be used in cereal crops. In the present study a novel collection of specific monoclonal antibodies has been produced using different immunizing haptens based on a carboxy-functionalized identical spacer arm attached to alternativ...detailed

Electrochemical determination of Picoxystrobin (cas 117428-22-5) on boron-doped diamond electrode: Square-wave voltammetry versus BIA-multiple pulse amperometry07/19/2019

This article reports and compares the performance of two new electrochemical methods for the determination of picoxystrobin (a strobilurin-class fungicide). The methods were square-wave voltammetry (SWV) and batch-injection analysis (BIA) with multiple-pulse amperometric detection, both employin...detailed

Determination of the fungicide Picoxystrobin (cas 117428-22-5) using anodic stripping voltammetry on a metal film modified glassy carbon electrode07/17/2019

Differential pulse anodic stripping voltammetry was used for trace determination of picoxystrobin in urine and water samples. Experimental conditions have been optimized and the measurement cycle started with the application of a deposition potential at −700 mV, during 60 s, for the in situ form...detailed

Thiamethoxam and Picoxystrobin (cas 117428-22-5) reduce the survival and overload the hepato-nephrocitic system of the Africanized honeybee07/16/2019

Apis mellifera perform important pollination roles in agroecosystems. However, there is often intensive use of systemic pesticides in crops, which can be carried to the colony by forage bees through the collection of contaminated pollen and nectar. Inside the colony, pollen loads are stored by b...detailed

Soil microorganisms' carbon transformation test for Picoxystrobin (cas 117428-22-5) 25% SC (w/v) in loamy sand soil07/15/2019

The effect of Picoxystrobin 25% SC on soil microorganisms (carbon transformation) was assessed in a test that measured induced respiration rate following the application of Picoxystrobin 25% SC to soil. Picoxystrobin 25% SC was incubated in loamy sand soil over a period of 28 days for the carbon...detailed

Relevant articles and documents

Preparation method of picoxystrobin

The invention belongs to the technical field of bactericides, and particularly relates to a preparation method of picoxystrobin. The invention provides a preparation method of picoxystrobin, which comprises the following steps: mixing 2-(6-trifluoromethylpyridine-2-yloxymethyl) methyl phenylacetate, acetic anhydride and trimethyl orthoformate, and carrying out condensation reaction to obtain the picoxystrobin. According to the invention, 2-(6-trifluoromethylpyridine-2-yloxymethyl) methyl phenylacetate, acetic anhydride and trimethyl orthoformate are used as raw materials, and the 2-(6-trifluoromethylpyridine-2-yloxymethyl) methyl phenylacetate and trimethyl orthoformate are subjected to a condensation reaction under the action of acetic anhydride to obtain picoxystrobin; and acetic anhydride can react with a condensation reaction byproduct to reduce the content of the condensation reaction byproduct, promote the condensation reaction and improve the yield of picoxystrobin. The preparation method provided by the invention is simple in process, mild in reaction condition, low in production cost and beneficial to industrial production.

Preparation method of picoxystrobin

The invention provides a preparation method of picoxystrobin. The preparation method includes the following steps: reacting an alkali metal salt of 2-hydroxy-6-trifluoromethylpyridine with (E)-3-methoxy-2-(2-halomethylphenyl)-2-methyl acrylate in a solvent to obtain the picoxystrobin, wherein the alkali metal salt of the 2-hydroxy-6-trifluoromethylpyridine is prepared by a hydrolysis reaction of 2-halo-6-trifluoromethylpyridine and alkali metal hydroxide. The preparation method provided by the invention saves the use of an acid binding agent in a condensation step and avoids tedious steps suchas acidification and drying in the hydrolysis reaction. After two steps of separation, the total yield is over 82%, and the product content is 97%-98%. A by-product is only a single inorganic salt, which reduces the equipment cost of solvent recovery and saves the use of acid and alkali, thereby reducing the material cost. The preparation method is suitable for industrial production and can generate high economic benefit.

Silver-Catalyzed Olefination of Acetals and Ketals with Diazoesters to β-Alkoxyacrylates

The first silver-catalyzed reaction of acetals or ketals with diazoesters leading to trisubstituted or tetrasubstituted β-alkoxyacrylates is now reported. A broad range of acetals and ketals bearing different substituents is compatible with this protocol and thus provides an attractive approach for the synthesis of complex β-alkoxyacrylates. The power of this method was further demonstrated by the successful synthesis of picoxystrobin, which is one of the most popular agricultural fungicides commercialized by Dupont.