Folpet

Folpet
Names
	Preferred IUPAC name 2-[(trichloromethyl)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^[update] 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. 22 (1). Stellenbosch University: 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. 52 (1). Annual Reviews: 175–195. doi:10.1146/annurev-phyto-102313-050158. ISSN 0066-4286. PMID 24848413. S2CID 36554883.

[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. 22 (1). Stellenbosch University: 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. 52 (1). Annual Reviews: 175–195. doi:10.1146/annurev-phyto-102313-050158. ISSN 0066-4286. PMID 24848413. S2CID 36554883.

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