Pyraclostrobin

Last updated
Pyraclostrobin
Pyraclostrobine.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 605-747-1
KEGG
PubChem CID
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:
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
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 [1] [2] [3] [4] fungicide [5] [6] [7] [8] used in agriculture. [8] Among the QoIs, it lies within the strobilurin chemical class. [9] [8]

Contents

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:

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

  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

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