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
ChemSpider	8288
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

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.
2. "Folpet: the essential multi-site fungicide". ADAMA UK. 2019-12-11. Retrieved 2021-03-13.
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.
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. Bibcode:2014AnRvP..52..175B. doi: 10.1146/annurev-phyto-102313-050158 . ISSN   0066-4286. PMID   24848413. S2CID   36554883.