Folpet

Folpet
Names
	Preferred IUPAC name 2-[(Tricloromethyl)sulfanyl]-1H-isoindole-1,3(2H)-dione
	Other names N-(Trichloromethylthio)phthalimide, Orthophaltan, Phaltan, Faltan, Folpan, Faltex, Folpex
Identifiers
CAS Number	133-07-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82019;
ChEMBL	ChEMBL1883819;
ECHA InfoCard	100.004.627
EC Number	205-088-6;
KEGG	C18860;
PubChem CID	8607;
RTECS number	TI5685000;
UNII	X5NFK36917;
UN number	3077 2588
CompTox Dashboard (EPA)	DTXSID0021385 ;
	InChI InChI=1S/C9H4Cl3NO2S/c10-9(11,12)16-13-7(14)5-3-1-2-4-6(5)8(13)15/h1-4H Key: HKIOYBQGHSTUDB-UHFFFAOYSA-N;
	SMILES C1=CC=C2C(=C1)C(=O)N(C2=O)SC(Cl)(Cl)Cl;
Properties
Chemical formula	C9H4Cl3NO2S
Molar mass	296.55 g·mol−1
Appearance	white solid
Density	1.72 g/cm3
Melting point	177 °C (351 °F; 450 K) (decomp.)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H317, H319, H332, H351, H400
Precautionary statements	P201, P202, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P333+P313, P337+P313, P363, P391, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Folpet is the tradename for the organic compound with the formula C₆H₄(CO)₂NSCCl₃. It is a fungicide derived from phthalimide (C₆H₄(CO)₂N-) and trichloromethylsulfenyl chloride. The compound is white although commercial samples can appear brownish. It is structurally related to Captan, which is also a trichloromethylsulfenyl-containing fungicide.[1]

Resistance

As of December 2019 folpet resistance is still unheard of due to its multiple effects.[2] However, in 2001 some degree of cross-resistance was reported in iprodione-resistant South African Botrytis cinerea on grape.[3][4]

References

Franz Müller; Peter Ackermann; Paul Margot (2012). "Fungicides, Agricultural, 2. Individual Fungicides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o12_o06. ISBN 978-3-527-30673-2.
"Folpet: the essential multi-site fungicide". ADAMA UK. 2019-12-11. Retrieved 2021-03-13.
Fourie, P.H.; Holz, G. (2001). "Incomplete Cross-Resistance to Folpet and Iprodione in Botrytis cinerea from Grapevine in South Africa". South African Journal of Enology & Viticulture. Stellenbosch University. 22 (1): 3-7. doi:10.21548/22-1-2158. ISSN 2224-7904. S2CID 56014315.
Bosch, Frank van den; Oliver, Richard; Berg, Femke van den; Paveley, Neil (2014-08-04). "Governing Principles Can Guide Fungicide-Resistance Management Tactics". Annual Review of Phytopathology. Annual Reviews. 52 (1): 175–195. doi:10.1146/annurev-phyto-102313-050158. ISSN 0066-4286. PMID 24848413. S2CID 36554883.

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[Ullmann-1] Franz Müller; Peter Ackermann; Paul Margot (2012). "Fungicides, Agricultural, 2. Individual Fungicides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o12_o06. ISBN 978-3-527-30673-2.

[ADAMA-2] "Folpet: the essential multi-site fungicide". ADAMA UK. 2019-12-11. Retrieved 2021-03-13.

[Fourie-Holz-2001-3] Fourie, P.H.; Holz, G. (2001). "Incomplete Cross-Resistance to Folpet and Iprodione in Botrytis cinerea from Grapevine in South Africa". South African Journal of Enology & Viticulture. Stellenbosch University. 22 (1): 3-7. doi:10.21548/22-1-2158. ISSN 2224-7904. S2CID 56014315.

[Bosch-et-al-2014-4] Bosch, Frank van den; Oliver, Richard; Berg, Femke van den; Paveley, Neil (2014-08-04). "Governing Principles Can Guide Fungicide-Resistance Management Tactics". Annual Review of Phytopathology. Annual Reviews. 52 (1): 175–195. doi:10.1146/annurev-phyto-102313-050158. ISSN 0066-4286. PMID 24848413. S2CID 36554883.