S-Ethyl dipropylthiocarbamate

S-Ethyl dipropylthiocarbamate (EPTC) is a selective herbicide used for pre-emergent control of certain grasses and broadleaf weeds in Australia and the United States.^[3][4] It was introduced in 1957.^[5]

S-Ethyl dipropylthiocarbamate

Names
Preferred IUPAC name S-Ethyl N,N-dipropylcarbamothioate
Other names EPTC Eptam Epthame S-Ethyl-N,N-dipropylthiocarbamate S-Ethyl N,N-dipropylcarbamothioate Carbamic acid, dipropylthio-, S-ethyl ester S-Ethyl dipropylcarbamothioate
Identifiers
CAS Number	759-94-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:4738
ChEMBL	ChEMBL1371350
ChemSpider	12428 N
ECHA InfoCard	100.010.976
EC Number	212-073-8
KEGG	C11081
PubChem CID	12968
UNII	R7PI3287F4
UN number	2902 2992
CompTox Dashboard (EPA)	DTXSID1024091
InChI InChI=1S/C9H19NOS/c1-4-7-10(8-5-2)9(11)12-6-3/h4-8H2,1-3H3 Key: GUVLYNGULCJVDO-UHFFFAOYSA-N
SMILES N(C(SCC)=O)(CCC)CCC
Properties
Chemical formula	C9H19NOS
Molar mass	189.32 g·mol−1
Appearance	light yellow liquid[1]
Odor	Aromatic, Characteristic[1]
Density	955 kg/m3 at 30°C[2]
Melting point	<25°C (<77°F) [2]
Boiling point	232 °C (450 °F; 505 K) [2]
Solubility in water	375 mg/L[1]
Solubility in [[acetone, ethanol, isopropanol, benzene, xylene]]	miscible[1]
Vapor pressure	3.2 Pa[1]
Viscosity	5.2 mm2/s
Hazards
GHS labelling:
Pictograms
Hazard statements	H302[3]
Flash point	116 °C (241 °F; 389 K)
Autoignition temperature	260 °C (500 °F; 533 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	916 mg/kg (rat, oral)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

EPTC can be applied pre-emergently or post-emergently and its effectiveness does not depend on post-application rainfall. The herbicide takes effect quickly after application. It is registered in every US state.^[6] It should be sprayed when the soil is well worked and dry, to allow good mixing and incorporation. It can be stored at temperatures as low as -50 °F.^[7]

It is not persistent in soil, having a half-life of about 6 days.^[1]

Use

EPTC is applied at rates of 2 to 7.5 lbs/ac in the US, or 2.5-5 kg/ha in Australia, measured by active ingredient. It is typically sold as an emulsifiable concentrate, of 70% of more s-ethyl dipropylthiocarbamate,^[8][9] or as granules.^[5]

In the United States, EPTC is registered for use on alfalfa, almonds, beans, birdsfoot trefoil, clovers, lespedeza, sainfoin, citrus nursery stock and plantings, cotton, grass, fallow, pine seedlings, potatoes, safflower, sugar beets, sunflower, tomatoes and walnuts.^[8]

In Australia, EPTC is used on beans, potatoes, maize, sweet corn, safflower, rapeseed, sunflower, lucerne, duboisia, lotus, non-crop situations and grass.^[9]

It has been sold under the tradenames Eradicane, Eptam, Genep and Shortstop. The long-running "Eptam" trademark is of the Stauffer Chemical Company.^[7]