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)-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]

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, 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]

References

Fernández-Ortuño, Dolores; Chen, Fengping; Schnabel, Guido (2012). "Resistance to Pyraclostrobin and Boscalid in Botrytis cinerea Isolates from Strawberry Fields in the Carolinas". Plant Disease. American Phytopathological Society. 96 (8): 1198–1203. doi:10.1094/pdis-12-11-1049-re. ISSN 0191-2917. PMID 30727059. S2CID 73440417.
Weber, Roland W. S. (2011). "Resistance of Botrytis cinerea to Multiple Fungicides in Northern German Small-Fruit Production". Plant Disease. American Phytopathological Society. 95 (10): 1263–1269. doi:10.1094/pdis-03-11-0209. ISSN 0191-2917. PMID 30731691. S2CID 73436385.
Amiri, A.; Heath, S. M.; Peres, N. A. (2013). "Phenotypic Characterization of Multifungicide Resistance in Botrytis cinerea Isolates from Strawberry Fields in Florida". Plant Disease. American Phytopathological Society. 97 (3): 393–401. doi:10.1094/pdis-08-12-0748-re. ISSN 0191-2917. PMID 30722364. S2CID 73422752.
Avenot, H.; Morgan, D. P.; Michailides, T. J. (2007-09-16). "Resistance to pyraclostrobin, boscalid and multiple resistance to Pristine® (pyraclostrobin + boscalid) fungicide in Alternaria alternata causing alternaria late blight of pistachios in California". Plant Pathology. British Society for Plant Pathology/Wiley-Blackwell. 57 (1): 135–140. doi:10.1111/j.1365-3059.2007.01701.x. ISSN 0032-0862. S2CID 83947838.
"Pyraclostrobin". System of Registries. United States Environmental Protection Agency.
Chambers, Michael. "175013-18-0 - HZRSNVGNWUDEFX-UHFFFAOYSA-N - Pyraclostrobin [ISO:BSI] - Similar structures search, synonyms, formulas, resource links, and other chemical information". ChemIDplus. National Library of Medicine, US NIH. Retrieved 2021-03-02.
"Preferred Substance Name: PYRACLOSTROBIN UNII: DJW8M9OX1H". Substance Registration System. US Food and Drug Administration. Retrieved 2021-03-02.
"Pyraclostrobin". PubChem. NCBI, NLM, US NIH. Retrieved 2021-03-02.
Declercq, Bernard. "Pyraclostrobin (210)" (PDF). Épinay-sur-Orge, France: UN FAO (Food and Agriculture Organization of the United Nations.
"2017 Pesticide Use Map - Pyraclostrobin". Water Resources. United States Geological Survey (USGS). Retrieved 2021-03-02.
"2017 Pesticide Use Map - Pyraclostrobin". Water Resources. United States Geological Survey (USGS). Retrieved 2021-03-02.
"Acute Pesticide Poisoning Associated with Pyraclostrobin Fungicide --- Iowa, 2007". United States Centers for Disease Control and Prevention. 2008-01-04. Retrieved 2021-03-02.
Health Risk Assessment Unit (June 2016). "Toxicological Summary for: Pyraclostrobin" (PDF). Environmental Health Division, Minnesota Department of Health.