Dimethenamid - Misplaced Pages

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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
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:81789
ChemSpider	82842
ECHA InfoCard	100.121.887
KEGG	C18499
PubChem CID	91744
RTECS number	AB5444200
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,5-6H2,1-4H3Key: JLYFCTQDENRSOL-UHFFFAOYSA-N InChI=1/C12H18ClNO2S/c1-8-7-17-10(3)12(8)14(11(15)5-13)9(2)6-16-4/h7,9H,5-6H2,1-4H3Key: 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/cm
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Xn (harmful)
Flash point	151 °C (304 °F; 424 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

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.

References

Dimethenamid at Sigma-Aldrich
Material Safety Data Sheet from BASF
Dimethenamid at AlanWood.net
2000-2001 Pesticide Market Estimates, U.S. Environmental Protection Agency
Crawford, J.J.; G. K. Sims; F. W. Simmons; L. M. Wax; D. L. Freedman (2002). "Dissipation of the herbicide (14C) Dimethenamid under anaerobic aquatic conditions in flooded soil microcosms". J. Agric. Food. Chem. 50 (6): 61483–1491. {{cite journal}}: |access-date= requires |url= (help)

Pest control: herbicides

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