Pyraclostrobin (original) (raw)

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Agricultural fungicide, QoI, strobilurin

Pyraclostrobin
Names
IUPAC name Methyl _N_-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-_N_-methoxycarbamate
Other namesPyraclostrobine
Identifiers
CAS Number 175013-18-0
3D model (JSmol) Interactive image
ChEBI CHEBI:78780
ChEMBL ChEMBL519873
ChemSpider 4928348
ECHA InfoCard 100.125.533 Edit this at Wikidata
EC Number 605-747-1
KEGG C18561
PubChem CID 6422843
UNII DJW8M9OX1H
CompTox Dashboard (EPA) DTXSID7032638 Edit this at Wikidata
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,13H2,1-2H3Key: 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 GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
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

Chemical compound

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]

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]

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

Resistant populations have been identified in:

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

Off-target toxicity

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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]

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

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

  1. ^ a b c d 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. ^ a b c d e f g h i 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. ^ a b c d 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. ^ a b c d 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.
  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.
  8. ^ a b c d e f g "Pyraclostrobin". PubChem. NCBI, NLM, US NIH. Retrieved 2021-03-02.
  9. ^ a b c 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.