Pyraclostrobin

Pyraclostrobin is a quinone outside inhibitor (Q_oI)-type^[1][2][3][4] fungicide^[5][6][7][8] used in agriculture.^[8] Among the Q_oIs, it lies within the strobilurin chemical class.^[9][8]

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

Use

Pyraclostrobin is used to protect Fragaria,^[1][2][3] Rubus idaeus,^[2] Vaccinium corymbosum,^[2] Ribes rubrum,^[2] Ribes uva-crispa,^[2] blackberry (various Rubus spp.),^[2] and Pistachio vera.^[4]

Target pathogens

Pyraclostrobin is used against Botrytis cinerea^[1][2][3] and Alternaria alternata.^[4]

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.^[1]
• Botrytis cinerea on Fragaria, Rubus idaeus, Vaccinium corymbosum, Ribes rubrum, Ribes uva-crispa, and blackberry (various Rubus spp.) in Northern Germany.^[2]
• Botrytis cinerea on Fragaria in Florida.^[3]
• Alternaria alternata on Pistachio vera in California.^[4]

Geography of use

United States

Pyraclostrobin was widely used throughout the United States As of 2017^[update], but especially in the Upper Midwest.^[10][11]

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^[12] of eyes and skin.^[8] It does cause some degree of reproductive and developmental failure in mammals^[13] but does not absorb well through the skin.^[8] It is likely to bioaccumulate in aquatic organisms.^[8]

Residues in diet

Pyraclostrobin does not accumulate in foods to a significant degree.^[9]

Biodegradability

Pyraclostrobin is described by one source as not very biodegradable,^[9] and by another as possibly significantly biodegradable.^[8]