Dimethenamid

Dimethenamid

Names
IUPAC name (RS)-2-Chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide
Other names Frontier Herbicide Dimethenamid-P ((S)-isomer)
Identifiers
CAS Number	87674-68-8 Y
ChEBI	CHEBI:81789 N
ChemSpider	82842 Y
Jmol 3D model	Interactive image Interactive image
KEGG	C18499 Y
PubChem	91744
RTECS number	AB5444200
InChI InChI=1S/C12H18ClNO2S/c1-8-7-17-10(3)12(8)14(11(15)5-13)9(2)6-16-4/h7,9H,5-6H2,1-4H3 Y Key: JLYFCTQDENRSOL-UHFFFAOYSA-N Y InChI=1/C12H18ClNO2S/c1-8-7-17-10(3)12(8)14(11(15)5-13)9(2)6-16-4/h7,9H,5-6H2,1-4H3 Key: JLYFCTQDENRSOL-UHFFFAOYAR
SMILES CC1=CSC(=C1N(C(C)COC)C(=O)CCl)C ClCC(=O)N(c1c(scc1C)C)C(COC)C
Properties
Chemical formula	C12H18ClNO2S
Molar mass	275.79 g/mol
Appearance	Tan to brown liquid
Density	1.141 g/cm3
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Dimethenamid is a widely used herbicide. In 2001, about 7 million pounds of dimethenamid were used in the United States. Dimethenamid is registered for control of annual grasses, certain annual broadleaf weeds and sedges in field corn, seed corn, popcorn and soybeans. Supplemental labeling also allows use on sweet corn, grain sorghum, dry beans and peanuts. In registering dimethinamide (SAN 582H/Frontier), EPA concluded that the primary means of dissipation of dimethenamid applied to the soil surface is photolysis, whereas below the surface loss was due largely to microbial metabolism. The herbicide was found to undergo anaerobic microbial degradation under denitrifying, iron-reducing, sulfate-reducing, or methanogenic conditions. In that study, more than half of the herbicide carbon (based on 14C-labeling) added was found to be incorporated irreversibly into soil-bound residue.