Pyraclostrobin
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| Names | |
|---|---|
| IUPAC name
Methyl N-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-N-methoxycarbamate | |
| Other names
Pyraclostrobine | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.125.533 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C19H18ClN3O4 | |
| Molar mass | 387.82 g·mol−1 |
| Hazards | |
| GHS labelling: | |
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| 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).
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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]
Use
[edit]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
[edit]Pyraclostrobin is used against Botrytis cinerea[1][2][3] and Alternaria alternata.[4]
Resistance
[edit]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
[edit]United States
[edit]Pyraclostrobin was widely used throughout the United States as of 2017, but especially in the Upper Midwest.[10][11]
Off-target toxicity
[edit]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
[edit]Pyraclostrobin does not accumulate in foods to a significant degree.[9]
Biodegradability
[edit]Pyraclostrobin is described by one source as not very biodegradable,[9] and by another as possibly significantly biodegradable.[8]
References
[edit]- 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.
- 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.
- 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.
- 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.
- ↑ "Pyraclostrobin". System of Registries. United States Environmental Protection Agency.[dead link]
- ↑ 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.[dead link]
- 1 2 3 4 5 6 7 "Pyraclostrobin". PubChem. NCBI, NLM, US NIH. Retrieved 2021-03-02.
- 1 2 3 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.
Further reading
[edit]- "CID 5327095". PubChem. NCBI, NLM, US NIH. Retrieved 2021-03-02.
- "Pyraclostrobine". NIST WebBook. National Institute of Standards and Technology. Retrieved 2021-03-02.