Pyraclostrobin

Pyraclostrobin

Names
IUPAC name Methyl N-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-N-methoxycarbamate
Other names Pyraclostrobine
Identifiers
CAS Number	175013-18-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:78780
ChEMBL	ChEMBL519873
ChemSpider	4928348
ECHA InfoCard	100.125.533
EC Number	605-747-1
KEGG	C18561
PubChem CID	6422843
UNII	DJW8M9OX1H
CompTox Dashboard (EPA)	DTXSID7032638
InChI InChI=1S/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 Key: HZRSNVGNWUDEFX-UHFFFAOYSA-N
SMILES COC(=O)N(C1=CC=CC=C1COC2=NN(C=C2)C3=CC=C(C=C3)Cl)OC
Properties
Chemical formula	C19H18ClN3O4
Molar mass	387.82 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H315, H331, H335, H410
Precautionary statements	P261, P264, P271, P273, P280, P302+P352, P304+P340, P311, P312, P321, P332+P313, P362, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Pyraclostrobin is a quinone outside inhibitor (Q_oI)-typefungicide used in agriculture. Among the Q_oIs, it lies within the strobilurin chemical class.

Use

Pyraclostrobin is used to protect Fragaria,Rubus idaeus,Vaccinium corymbosum,Ribes rubrum,Ribes uva-crispa,blackberry (various Rubus spp.), and Pistachio vera.

Target pathogens

Pyraclostrobin is used against Botrytis cinerea and Alternaria alternata.

Resistance

Resistant populations have been identified in:

• Botrytis cinerea on Fragaria in the Carolinas, conferred by the G143A mutation in the partial cytochrome b (CYTB) gene.
• Botrytis cinerea on Fragaria, Rubus idaeus, Vaccinium corymbosum, Ribes rubrum, Ribes uva-crispa, and blackberry (various Rubus spp.) in Northern Germany.
• Botrytis cinerea on Fragaria in Florida.
• Alternaria alternata on Pistachio vera in California.

Geography of use

United States

Pyraclostrobin was widely used throughout the United States As of 2017, but especially in the Upper Midwest.

Off-target toxicity

Although toxic, and recommended to be avoided by humans, pyraclostrobin is of temporary and low toxicity, that is to say it is merely an irritant of eyes and skin. It does cause some degree of reproductive and developmental failure in mammals but does not absorb well through the skin. It is likely to bioaccumulate in aquatic organisms.

Residues in diet

Pyraclostrobin does not accumulate in foods to a significant degree.

Biodegradability

Pyraclostrobin is described by one source as not very biodegradable, and by another as possibly significantly biodegradable.

Further reading

• "CID 5327095". PubChem. NCBI, NLM, US NIH. Retrieved 2021-03-02.
• "Pyraclostrobine". NIST WebBook. National Institute of Standards and Technology. Retrieved 2021-03-02.