Dimethenamid

Dimethenamid^[1][2]

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
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:81789 N
ChemSpider	82842 Y
ECHA InfoCard	100.121.887
EC Number	618-045-5
KEGG	C18499 Y
PubChem CID	91744
RTECS number	AB5444200
UNII	8504Z6C4XZ Y
CompTox Dashboard (EPA)	DTXSID4032376
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
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Xn (harmful)
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H317, H332, H410, H411
Precautionary statements	P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P321, P330, P333+P313, P363, P391, P501
Flash point	151 °C (304 °F; 424 K)
Safety data sheet (SDS)	MSDS from BASF
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 belonging to the chloroacetamide class (group 15). Group 15 herbicides inhibit synthesis of certain long-chain fatty acids reducing availability of ipids, proteins, and lignin for the plant growth.^[3] In 2001, about 7 million pounds (3,200 t) of dimethenamid were used in the United States.^[4] 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.^[5] 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.

References