Pyraclostrobin

Pyraclostrobin
Names
IUPAC name
Methyl N-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-N-methoxycarbamate
Other names
Pyraclostrobine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.125.533 Edit this at Wikidata
EC Number
  • 605-747-1
KEGG
UNII
  • 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
  • COC(=O)N(C1=CC=CC=C1COC2=NN(C=C2)C3=CC=C(C=C3)Cl)OC
Properties
C19H18ClN3O4
Molar mass 387.82 g·mol−1
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H315, H331, H335, H410
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).

Pyraclostrobin is a quinone outside inhibitor (QoI)-type fungicide used in agriculture. Among the QoIs, 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:

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.

References

  1. 1 2 3 4 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. 96 (8). American Phytopathological Society: 1198–1203. doi:10.1094/pdis-12-11-1049-re. ISSN 0191-2917. PMID 30727059. S2CID 73440417.
  2. 1 2 3 4 5 6 7 8 9 Weber, Roland W. S. (2011). "Resistance of Botrytis cinerea to Multiple Fungicides in Northern German Small-Fruit Production". Plant Disease. 95 (10). American Phytopathological Society: 1263–1269. doi:10.1094/pdis-03-11-0209. ISSN 0191-2917. PMID 30731691. S2CID 73436385.
  3. 1 2 3 4 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. 97 (3). American Phytopathological Society: 393–401. doi:10.1094/pdis-08-12-0748-re. ISSN 0191-2917. PMID 30722364. S2CID 73422752.
  4. 1 2 3 4 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. 57 (1). British Society for Plant Pathology/Wiley-Blackwell: 135–140. doi:10.1111/j.1365-3059.2007.01701.x. ISSN 0032-0862. S2CID 83947838.
  5. ↑ "Pyraclostrobin". System of Registries. United States Environmental Protection Agency.[dead link]
  6. ↑ 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.
  7. ↑ "Preferred Substance Name: PYRACLOSTROBIN UNII: DJW8M9OX1H". Substance Registration System. US Food and Drug Administration. Retrieved 2021-03-02.[dead link]
  8. 1 2 3 4 5 6 7 "Pyraclostrobin". PubChem. NCBI, NLM, US NIH. Retrieved 2021-03-02.
  9. 1 2 3 Declercq, Bernard. "Pyraclostrobin (210)" (PDF). Épinay-sur-Orge, France: UN FAO (Food and Agriculture Organization of the United Nations.
  10. ↑ "2017 Pesticide Use Map - Pyraclostrobin". Water Resources. United States Geological Survey (USGS). Retrieved 2021-03-02.
  11. ↑ "2017 Pesticide Use Map - Pyraclostrobin". Water Resources. United States Geological Survey (USGS). Retrieved 2021-03-02.
  12. ↑ "Acute Pesticide Poisoning Associated with Pyraclostrobin Fungicide --- Iowa, 2007". United States Centers for Disease Control and Prevention. 2008-01-04. Retrieved 2021-03-02.
  13. ↑ Health Risk Assessment Unit (June 2016). "Toxicological Summary for: Pyraclostrobin" (PDF). Environmental Health Division, Minnesota Department of Health.

Further reading