Azoxystrobin

Basic Info

Common NameAzoxystrobin(F05029)
2D Structure
Description

Azoxystrobin (brand name Amistar, Syngenta) is a fungicide commonly used in agriculture. Azoxystrobin possesses the broadest spectrum of activity of all known antifungals. The substance is used as an active agent protecting plants and fruit/vegetables from fungal diseases. Azoxystrobin binds very tightly to the Qo site of Complex III of the mitochondrial electron transport chain, thereby ultimately preventing the generation of ATP. Azoxystrobin is widely used in farming, particularly in wheat farming.

FRCD IDF05029
CAS Number131860-33-8
PubChem CID3034285
FormulaC22H17N3O5
IUPAC Name

methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]-3-methoxyprop-2-enoate

InChI Key

WFDXOXNFNRHQEC-GHRIWEEISA-N

InChI

InChI=1S/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+

Canonical SMILES

COC=C(C1=CC=CC=C1OC2=NC=NC(=C2)OC3=CC=CC=C3C#N)C(=O)OC

Isomeric SMILES

CO/C=C(\C1=CC=CC=C1OC2=NC=NC(=C2)OC3=CC=CC=C3C#N)/C(=O)OC

Synonyms
        
            Amistar
        
            UNII-NYH7Y08IPM
        
            Azoxystrobin
        
            131860-33-8
        
            Bankit
        
            Heritage
        
            Quadris
        
            Icia-5504
        
            HSDB 7017
        
            TCMDC-125883
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenyl-beta-methoxyacrylates
Intermediate Tree NodesNot available
Direct ParentPhenyl-beta-methoxyacrylates
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsPhenyl-beta-methoxyacrylate - Diaryl ether - Benzonitrile - Phenoxy compound - Phenol ether - Styrene - Pyrimidine - Methyl ester - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Vinylogous ester - Heteroaromatic compound - Carboxylic acid ester - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Ether - Monocarboxylic acid or derivatives - Carbonitrile - Nitrile - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organic oxide - Hydrocarbon derivative - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenyl-beta-methoxyacrylates. These are aromatic compounds containing a methyl-3-methoxyacrylate moiety that carries a benzyl group at the C-alpha carbon.

Properties

Property NameProperty Value
Molecular Weight403.394
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count8
Rotatable Bond Count8
Complexity646
Monoisotopic Mass403.117
Exact Mass403.117
XLogP3.7
Formal Charge0
Heavy Atom Count30
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Ware PotatoesBritain0.05mg/kg
HopBritain20mg/kg
TeaBritain0.1mg/kg
Early PotatoesBritain0.05mg/kg
Other OilseedsBritain0.05mg/kg
Hemp SeedBritain0.05mg/kg
Cotton SeedBritain0.05mg/kg
Mustard SeedBritain0.05mg/kg
Soya BeanBritain0. 5mg/kg
Rape SeedBritain0. 5mg/kg
Sunflower SeedBritain0.05mg/kg
Sesame SeedBritain0.05mg/kg
Poppy SeedBritain0.05mg/kg
PeanutsBritain0.05mg/kg
LinseedBritain0.05mg/kg
Other PulsesBritain0.1mg/kg
LupinsBritain0.1mg/kg
PeasBritain0.1mg/kg
LentilsBritain0.1mg/kg
BeansBritain0.1mg/kg

References

TitleJournalDatePubmed ID
A return to the genetic heritage of durum wheat to cope with drought heightenedby climate change.PLoS One2018 May 2429795584
Synthesis of new 4-aryloxy-N-arylanilines and their inhibitory activities againstsuccinate-cytochrome c reductase.Bioorg Med Chem Lett2018 May 129576509
Leaching and sorption of neonicotinoid insecticides and fungicides from seedcoatings.J Environ Sci Health B2018 Mar 429286873
Transfer of the Active Ingredients of Some Plant Protection Products fromRaspberry Plants to Beehives.Arch Environ Contam Toxicol2018 Jul29247388
Characterization of the Potent Odorants Contributing to the Characteristic Aroma of Beijing Douzhi by Gas Chromatography-Olfactometry, Quantitative Analysis, and Odor Activity Value.J Agric Food Chem2018 Jan 2429260548
Rapid analysis of fungicides in tea infusions using ionic liquid immobilizedfabric phase sorptive extraction with the assistance of surfactant fungicidesanalysis using IL-FPSE assisted with surfactant.Food Chem2018 Jan 1528873637
Transfer of plant protection products from raspberry crops of Laszka and Seedlingvarieties to beehives.Environ Monit Assess2018 Feb 1229435675
Comparison of a new air-assisted sprayer and two conventional sprayers in termsof deposition, loss to the soil and residue of azoxystrobin and tebuconazoleapplied to sunlit greenhouse tomato and field cucumber.Pest Manag Sci2018 Feb28898566
Dynamic residual pattern of azoxystrobin in Swiss chard with contribution tosafety evaluation.Biomed Chromatogr2018 Feb28921606
Environmental and human health risk indicators for agricultural pesticides inestuaries.Ecotoxicol Environ Saf2018 Apr 1529288903
Bioaccumulation and risk assessment of organochlorine pesticides in fish from aglobal biodiversity hotspot: iSimangaliso Wetland Park, South Africa.Sci Total Environ2018 Apr 1529186702
Identification and characterization of pesticide metabolites in Brassica species by liquid chromatography travelling wave ion mobility quadrupole time-of-flightmass spectrometry (UPLC-TWIMS-QTOF-MS).Food Chem2018 Apr 129120785
Fitness, Competitive Ability, and Mutation Stability of Isolates ofColletotrichum acutatum from Strawberry Resistant to QoI Fungicides.Phytopathology2018 Apr29135359
Liquid chromatography-tandem mass spectrometry method for simultaneousquantification of azoxystrobin and its metabolites, azoxystrobin free acid and2-hydroxybenzonitrile, in greenhouse-grown lettuce.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017Dec28934012
Impacts of dietary calcium, phytate, and phytase on inositol hexakisphosphatedegradation and inositol phosphate release in different segments of digestivetract of broilers.Poult Sci2017 Oct 128938789
Interactive effects of an insecticide and a fungicide on different organismgroups and ecosystem functioning in a stream detrital food web.Aquat Toxicol2017 May28324829
Tebuconazole and Azoxystrobin Residue Behaviors and Distribution in Field andCooked Peanut.J Agric Food Chem2017 Jun 728499340
Removal of six pesticide residues in cowpea with alkaline electrolysed water.J Sci Food Agric2017 Jun27633686
Pesticide residues in leafy vegetables and human health risk assessment in North Central agricultural areas of Chile.Food Addit Contam Part B Surveill2017 Jun28090975
Pesticide Chemical Research in Toxicology: Lessons from Nature.Chem Res Toxicol2017 Jan 1727715053